JP2010116545A - Polymer, rubber composition and tire using the same - Google Patents
Polymer, rubber composition and tire using the same Download PDFInfo
- Publication number
- JP2010116545A JP2010116545A JP2009230891A JP2009230891A JP2010116545A JP 2010116545 A JP2010116545 A JP 2010116545A JP 2009230891 A JP2009230891 A JP 2009230891A JP 2009230891 A JP2009230891 A JP 2009230891A JP 2010116545 A JP2010116545 A JP 2010116545A
- Authority
- JP
- Japan
- Prior art keywords
- styrene
- polymer
- weight
- rubber composition
- hydrocarbon group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 58
- 239000005060 rubber Substances 0.000 title claims abstract description 58
- 229920000642 polymer Polymers 0.000 title claims abstract description 55
- 239000000203 mixture Substances 0.000 title claims abstract description 50
- -1 nitrogen-containing compound Chemical class 0.000 claims abstract description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 239000003607 modifier Substances 0.000 claims abstract description 18
- 125000000524 functional group Chemical group 0.000 claims abstract description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 5
- 239000010703 silicon Substances 0.000 claims abstract description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000000377 silicon dioxide Substances 0.000 claims description 16
- 239000006229 carbon black Substances 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000446 fuel Substances 0.000 abstract description 20
- 229920002554 vinyl polymer Polymers 0.000 abstract description 8
- 239000004615 ingredient Substances 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 68
- 229920001084 poly(chloroprene) Polymers 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- 239000000178 monomer Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000006087 Silane Coupling Agent Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 150000002642 lithium compounds Chemical class 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000013329 compounding Methods 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920003244 diene elastomer Polymers 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 4
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 229920003052 natural elastomer Polymers 0.000 description 4
- 229920001194 natural rubber Polymers 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 239000005049 silicon tetrachloride Substances 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- MMZPUXVBQAQQDQ-UHFFFAOYSA-N triethoxy(2-pyridin-4-ylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=NC=C1 MMZPUXVBQAQQDQ-UHFFFAOYSA-N 0.000 description 4
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- OHDSHGBRKMRPHC-UHFFFAOYSA-N 2-(4-ethenylphenyl)-n,n-dimethylethanamine Chemical compound CN(C)CCC1=CC=C(C=C)C=C1 OHDSHGBRKMRPHC-UHFFFAOYSA-N 0.000 description 3
- WBUSESIMOZDSHU-UHFFFAOYSA-N 3-(4,5-dihydroimidazol-1-yl)propyl-triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCN=C1 WBUSESIMOZDSHU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- GRVAGTQLVKBPLL-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]azepane Chemical compound C1=CC(C=C)=CC=C1CCN1CCCCCC1 GRVAGTQLVKBPLL-UHFFFAOYSA-N 0.000 description 2
- LMAFWBCYAPNOFK-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]pyrrolidine Chemical compound C1=CC(C=C)=CC=C1CCN1CCCC1 LMAFWBCYAPNOFK-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- XLOUXCBUKZRSQG-UHFFFAOYSA-N 2-oxo-n-(3-trimethoxysilylpropyl)azepane-1-carboxamide Chemical compound CO[Si](OC)(OC)CCCNC(=O)N1CCCCCC1=O XLOUXCBUKZRSQG-UHFFFAOYSA-N 0.000 description 2
- IABJHLPWGMWHLX-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propyl-trimethoxysilane Chemical compound C1=CC=C2SC(CCC[Si](OC)(OC)OC)=NC2=C1 IABJHLPWGMWHLX-UHFFFAOYSA-N 0.000 description 2
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- WJUHASGUDSZAIJ-UHFFFAOYSA-N 4-[2-(4-ethenylphenyl)ethyl]morpholine Chemical compound C1=CC(C=C)=CC=C1CCN1CCOCC1 WJUHASGUDSZAIJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229920003049 isoprene rubber Polymers 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 description 2
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 2
- HMMPCBAWTWYFLR-UHFFFAOYSA-N n-pyridin-2-ylpyridin-2-amine Chemical compound C=1C=CC=NC=1NC1=CC=CC=N1 HMMPCBAWTWYFLR-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- XVZMLSWFBPLMEA-UHFFFAOYSA-N trimethoxy(2-pyridin-2-ylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=N1 XVZMLSWFBPLMEA-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- CGCQHMFVCNWSOV-UHFFFAOYSA-N (4-morpholin-4-ylphenyl)-phenylmethanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C1=CC=CC=C1 CGCQHMFVCNWSOV-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- ONILJRYQYWLXQU-UHFFFAOYSA-N 1,1-dioctyl-3-(3-triethoxysilylpropyl)urea Chemical compound CCCCCCCCN(CCCCCCCC)C(=O)NCCC[Si](OCC)(OCC)OCC ONILJRYQYWLXQU-UHFFFAOYSA-N 0.000 description 1
- SOAWOGBXWCCNFB-UHFFFAOYSA-N 1,1-dioctyl-3-(3-trimethoxysilylpropyl)urea Chemical compound CCCCCCCCN(CCCCCCCC)C(=O)NCCC[Si](OC)(OC)OC SOAWOGBXWCCNFB-UHFFFAOYSA-N 0.000 description 1
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 description 1
- HOBIHBQJHORMMP-UHFFFAOYSA-N 1,3-bis(3-triethoxysilylpropyl)urea Chemical compound CCO[Si](OCC)(OCC)CCCNC(=O)NCCC[Si](OCC)(OCC)OCC HOBIHBQJHORMMP-UHFFFAOYSA-N 0.000 description 1
- HSDGFGSXXVWDET-UHFFFAOYSA-N 1,3-bis(3-trimethoxysilylpropyl)urea Chemical compound CO[Si](OC)(OC)CCCNC(=O)NCCC[Si](OC)(OC)OC HSDGFGSXXVWDET-UHFFFAOYSA-N 0.000 description 1
- ZWAVGZYKJNOTPX-UHFFFAOYSA-N 1,3-diethylurea Chemical compound CCNC(=O)NCC ZWAVGZYKJNOTPX-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- GAIQQJIMVVUTQN-UHFFFAOYSA-N 1-(4-imidazol-1-ylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C=NC=C1 GAIQQJIMVVUTQN-UHFFFAOYSA-N 0.000 description 1
- AKQWEDMTPCAESO-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCOCC1 AKQWEDMTPCAESO-UHFFFAOYSA-N 0.000 description 1
- ODICSUWNOCWVPI-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)-4-phenylpiperazine Chemical compound C1CN(C=2C=CC=CC=2)CCN1CC1CO1 ODICSUWNOCWVPI-UHFFFAOYSA-N 0.000 description 1
- HNAGOQWONSUAQE-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)-4-pyridin-2-ylpiperazine Chemical compound C1CN(C=2N=CC=CC=2)CCN1CC1CO1 HNAGOQWONSUAQE-UHFFFAOYSA-N 0.000 description 1
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- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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- 229920001296 polysiloxane Polymers 0.000 description 1
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- 159000000001 potassium salts Chemical class 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
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- 239000011115 styrene butadiene Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- WDVUXWDZTPZIIE-UHFFFAOYSA-N trichloro(2-trichlorosilylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CC[Si](Cl)(Cl)Cl WDVUXWDZTPZIIE-UHFFFAOYSA-N 0.000 description 1
- LFBSOUVFURPMCL-UHFFFAOYSA-N triethoxy(3-pyrrol-1-ylpropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN1C=CC=C1 LFBSOUVFURPMCL-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- KLFNHRIZTXWZHT-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltrisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSCCC[Si](OCC)(OCC)OCC KLFNHRIZTXWZHT-UHFFFAOYSA-N 0.000 description 1
- HPEPIADELDNCED-UHFFFAOYSA-N triethoxysilylmethanol Chemical compound CCO[Si](CO)(OCC)OCC HPEPIADELDNCED-UHFFFAOYSA-N 0.000 description 1
- FTDRQHXSYGDMNJ-UHFFFAOYSA-N trimethoxy(3-pyrrol-1-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1C=CC=C1 FTDRQHXSYGDMNJ-UHFFFAOYSA-N 0.000 description 1
- MQGPKQPSPLQBBD-UHFFFAOYSA-N trimethoxy-[2-(2-pyridin-4-ylethylsulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)SCCC1=CC=NC=C1 MQGPKQPSPLQBBD-UHFFFAOYSA-N 0.000 description 1
- JSXKIRYGYMKWSK-UHFFFAOYSA-N trimethoxy-[2-(2-trimethoxysilylethyltetrasulfanyl)ethyl]silane Chemical compound CO[Si](OC)(OC)CCSSSSCC[Si](OC)(OC)OC JSXKIRYGYMKWSK-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- JTTSZDBCLAKKAY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSSSCCC[Si](OC)(OC)OC JTTSZDBCLAKKAY-UHFFFAOYSA-N 0.000 description 1
- FPKMSRRUOFZBQR-UHFFFAOYSA-N triphenoxymethylsilane Chemical compound O(C1=CC=CC=C1)C(OC1=CC=CC=C1)(OC1=CC=CC=C1)[SiH3] FPKMSRRUOFZBQR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L7/00—Compositions of natural rubber
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
Abstract
Description
本発明は、窒素含有重合体、該重合体を含み低燃費性およびウェットグリップ性能のバランスに優れたゴム組成物およびそれを用いたタイヤに関する。 The present invention relates to a nitrogen-containing polymer, a rubber composition containing the polymer and excellent in balance between fuel efficiency and wet grip performance, and a tire using the rubber composition.
近年省資源、省エネルギーに加えて、環境保護の立場から排出炭酸ガスの低減の社会的要求が強まっている。自動車に対しても排出炭酸ガスの低減を目的として、自動車の軽量化・電気エネルギーの利用等の様々な対応策が検討されている。自動車の共通の課題として、タイヤの転がり抵抗改善による燃費性能の向上が必要とされており、更に自動車に対しては、走行時の安全性向上の要求も強まっている。これら自動車の燃費性能及び安全性は使用されるタイヤの性能に負うところが大きく、自動車用のタイヤに対しては、省燃費性、操縦安定性、耐久性の改善要求が強まっている。これらのタイヤ特性は、タイヤの構造・使用材料等種々の要素に左右されるが、特に路面に接するトレッド部分に用いるゴム組成物の性能が低燃費性・安全性・耐久性等のタイヤ特性への寄与が大きい。このため、タイヤ用ゴム組成物の技術的改良が多く検討・提案され、実用化されている。 In recent years, in addition to saving resources and energy, social demands for reducing carbon dioxide emissions have been increasing from the standpoint of environmental protection. Various countermeasures such as reducing the weight of automobiles and using electric energy have been studied for the purpose of reducing carbon dioxide emissions from automobiles. As a common problem for automobiles, it is necessary to improve fuel efficiency by improving rolling resistance of tires. Further, there is an increasing demand for automobiles to improve safety during driving. The fuel efficiency and safety of these automobiles depend largely on the performance of the tires used, and there is an increasing demand for improvement in fuel economy, steering stability and durability for automobile tires. These tire characteristics depend on various factors such as the tire structure and materials used, but the performance of the rubber composition used for the tread portion in contact with the road surface is particularly suitable for tire characteristics such as fuel efficiency, safety and durability. The contribution of is large. For this reason, many technical improvements of rubber compositions for tires have been studied and proposed and put into practical use.
例えば、タイヤトレッドのゴム性能として、低燃費性向上にはヒステリシスロスが小さいこと、ウェットグリップ性能向上にはウェットスキッド抵抗性が高いことが要求されている。しかしながら、低ヒステリシスロスとウェットスキッド抵抗性との関係は相反するものであり、一つだけの性能向上では問題点の解決は難しいのが現状である。タイヤ用ゴム組成物の改良の代表的な手法は、使用する原材料の改良であり、SBRやBRに代表される原料ゴムの構造の改良、カーボンブラック・シリカ等の補強充填剤、加硫剤、可塑剤等の構造や組成の改良が行われている。 For example, as a rubber performance of a tire tread, it is required that hysteresis loss is small for improving fuel economy and wet skid resistance is high for improving wet grip performance. However, the relationship between low hysteresis loss and wet skid resistance is contradictory, and it is difficult to solve the problem with only one performance improvement. A typical method for improving the rubber composition for tires is improvement of raw materials used, improvement of the structure of raw rubber represented by SBR and BR, reinforcing filler such as carbon black and silica, vulcanizing agent, Improvements in the structure and composition of plasticizers and the like have been made.
ヒステリシスロスの小さいゴムを得るために、特許文献1では、ポリブタジエンゴム、スズ変性ポリブタジエンゴム、及び、他のゴムを含有するゴム成分からなるゴム組成物が提案されている。また、ウェットスキッド抵抗性が高いゴムを得るために、特許文献2では、ジエン系ゴムを有機ケイ素化合物により変性して得られた変性ジエン系ゴムを含む変性ジエン系ゴム組成物が提案されている。しかし近年では、環境問題からタイヤの低燃費性に対する要求はますます厳しくなっており、上記の方法では低燃費性およびウェットグリップ性能のバランスに対する要求を満たすことができていない。 In order to obtain a rubber having a small hysteresis loss, Patent Document 1 proposes a rubber composition comprising a rubber component containing polybutadiene rubber, tin-modified polybutadiene rubber, and other rubber. In order to obtain a rubber having high wet skid resistance, Patent Document 2 proposes a modified diene rubber composition containing a modified diene rubber obtained by modifying a diene rubber with an organosilicon compound. . However, in recent years, the demand for low fuel consumption of tires has become more severe due to environmental problems, and the above method cannot satisfy the demand for the balance between low fuel consumption and wet grip performance.
本発明は、前記課題を解決し、低燃費性とウェットグリップ性能に優れたタイヤを供することができるゴム組成物を提供することを目的とする。 An object of the present invention is to provide a rubber composition capable of solving the above-described problems and providing a tire excellent in fuel efficiency and wet grip performance.
本発明は、共役ジエン化合物および/または芳香族ビニル化合物と、下記一般式
で表される窒素含有化合物とを共重合して得られる重合体に関する。
The present invention includes a conjugated diene compound and / or an aromatic vinyl compound, and the following general formula:
It is related with the polymer obtained by copolymerizing with the nitrogen-containing compound represented by these.
上記重合体は、少なくとも一方の末端を窒素、酸素、ケイ素の中から選ばれる少なくとも一つの原子を含む官能基を有する変性剤で変性されていることが好ましい。 The polymer is preferably modified with a modifier having a functional group containing at least one atom selected from nitrogen, oxygen and silicon at least one terminal.
上記重合体における窒素含有化合物の含有量が0.05〜30重量%であることが好ましい。 The content of the nitrogen-containing compound in the polymer is preferably 0.05 to 30% by weight.
上記重合体の重量平均分子量Mwが1.0×105〜2.0×106であることが好ましい。 The weight average molecular weight Mw of the polymer is preferably 1.0 × 10 5 to 2.0 × 10 6 .
また、本発明は、上記重合体を含むゴム組成物に関する。 Moreover, this invention relates to the rubber composition containing the said polymer.
上記ゴム組成物において、ゴム成分100重量%の中に、上記重合体が5重量%以上含まれることが好ましい。 In the rubber composition, it is preferable that 5% by weight or more of the polymer is contained in 100% by weight of the rubber component.
上記ゴム組成物において、上記重合体を含むゴム成分100重量部に対して、カーボンブラックおよび/またはシリカを5〜150重量部含むことが好ましい。 The rubber composition preferably contains 5 to 150 parts by weight of carbon black and / or silica with respect to 100 parts by weight of the rubber component containing the polymer.
また、本発明は、上記ゴム組成物を用いたタイヤに関する。 The present invention also relates to a tire using the rubber composition.
本発明によれば、特定の窒素含有化合物を有する新規な重合体を含み、低燃費性およびウェットグリップ性能のバランスに優れたゴム組成物、および、該ゴム組成物を用いてなる上記特性を有するタイヤを提供することができる。 According to the present invention, a rubber composition including a novel polymer having a specific nitrogen-containing compound and having an excellent balance between low fuel consumption and wet grip performance, and the above-described characteristics using the rubber composition Tires can be provided.
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明の重合体は、共役ジエン化合物および/または芳香族ビニル化合物と、下記一般式
で表される窒素含有化合物とを共重合して得られる。
The polymer of the present invention comprises a conjugated diene compound and / or an aromatic vinyl compound, and the following general formula:
It is obtained by copolymerizing with a nitrogen-containing compound represented by the formula:
R0及びR8〜R14が脂肪族炭化水素基である場合、炭素数は1〜30であり、好ましくは1〜5である。また、R0及びR8〜R14が脂環族炭化水素基である場合、炭素数は3〜30であり、好ましくは3〜10である。更に、R0及びR8〜R14が芳香族炭化水素基である場合、炭素数は5〜30であり、好ましくは5〜10である。
また、R0及びR8〜R14は、水素又は炭素数1〜2の脂肪族炭化水素基であることが好ましい。
When R 0 and R 8 to R 14 are aliphatic hydrocarbon groups, the number of carbon atoms is 1 to 30, preferably 1 to 5. Moreover, when R < 0 > and R < 8 > -R < 14 > are alicyclic hydrocarbon groups, carbon number is 3-30, Preferably it is 3-10. Furthermore, when R < 0 > and R < 8 > -R < 14 > are aromatic hydrocarbon groups, carbon number is 5-30, Preferably it is 5-10.
R 0 and R 8 to R 14 are preferably hydrogen or an aliphatic hydrocarbon group having 1 to 2 carbon atoms.
R3は、水素又は炭素数1〜2の炭化水素基であることが好ましい。 R 3 is preferably hydrogen or a hydrocarbon group having 1 to 2 carbon atoms.
R4〜R7が脂肪族炭化水素基である場合、炭素数は1〜30であり、好ましくは1〜10である。また、R4〜R7が脂環族炭化水素基である場合、炭素数は3〜30であり、好ましくは3〜10である。更に、R4〜R7が芳香族炭化水素基である場合、炭素数は5〜30であり、好ましくは5〜10である。そして、R4〜R7が複素環基(芳香族複素環基を含む)である場合、環構成原子数は3〜30であり、好ましくは3〜10である。
また、R4〜R7は、脂肪族炭化水素基、芳香族炭化水素基又は複素環基であることが好ましく、脂肪族炭化水素基であることがより好ましい。
When R < 4 > -R < 7 > is an aliphatic hydrocarbon group, carbon number is 1-30, Preferably it is 1-10. Moreover, when R < 4 > -R < 7 > is an alicyclic hydrocarbon group, carbon number is 3-30, Preferably it is 3-10. Furthermore, when R < 4 > -R < 7 > is an aromatic hydrocarbon group, carbon number is 5-30, Preferably it is 5-10. And when R < 4 > -R < 7 > is a heterocyclic group (an aromatic heterocyclic group is included), the number of ring constituent atoms is 3-30, Preferably it is 3-10.
R 4 to R 7 are preferably an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a heterocyclic group, and more preferably an aliphatic hydrocarbon group.
lの値は、3〜10であり、好ましくは3〜7である。m及びnの値は、1〜9であり、好ましくは1〜6である。 The value of l is 3 to 10, preferably 3 to 7. The values of m and n are 1-9, preferably 1-6.
lの値は3〜10であるため、(CR8R9)は複数存在する。複数の(CR8R9)のそれぞれは同じであっても異なってもよい。同様に、mが2以上の場合、複数の(CR10R11)のそれぞれは同じであっても異なってもよく、nが2以上の場合、複数の(CR13R14)のそれぞれは同じであっても異なってもよい。 Since the value of l is 3 to 10, there are a plurality of (CR 8 R 9 ). Each of the plurality of (CR 8 R 9 ) may be the same or different. Similarly, when m is 2 or more, each of the plurality of (CR 10 R 11 ) may be the same or different, and when n is 2 or more, each of the plurality of (CR 13 R 14 ) is the same. Or different.
本明細書において、飽和形環形成部とは、飽和環基の一部であることを意味する。すなわち、上記一般式において、XとNとは飽和環基を構成し、ZとNとは飽和環基を構成する。 In this specification, the saturated ring-forming part means a part of a saturated ring group. That is, in the above general formula, X and N constitute a saturated ring group, and Z and N constitute a saturated ring group.
前記共役ジエン化合物としては、例えば1,3−ブタジエン、イソプレン、1,3−ペンタジエン、2,3−ジメチルブタジエン、2−フェニル−1,3−ブタジエン、1,3−ヘキサジエンなどが挙げられる。これらは単独で用いてもよく、2種以上を組み合わせて用いてもよいが、これらの中で、モノマーの入手容易性などの実用面の観点から1,3−ブタジエン、イソプレンが特に好ましい。 Examples of the conjugated diene compound include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethylbutadiene, 2-phenyl-1,3-butadiene, 1,3-hexadiene, and the like. These may be used singly or in combination of two or more. Among these, 1,3-butadiene and isoprene are particularly preferable from the viewpoint of practical use such as availability of monomers.
前記芳香族ビニル化合物としては、例えばスチレン、α−メチルスチレン、1−ビニルナフタレン、3−ビニルトルエン、エチルビニルベンゼン、ジビニルベンゼン、4−シクロヘキシルスチレン、2,4,6−トリメチルスチレンなどが挙げられる。これらは単独で用いてもよく、2種以上を組み合わせても用いてもよいが、これらの中で、モノマーの入手容易性などの実用面の観点からスチレンが特に好ましい。 Examples of the aromatic vinyl compound include styrene, α-methylstyrene, 1-vinylnaphthalene, 3-vinyltoluene, ethylvinylbenzene, divinylbenzene, 4-cyclohexylstyrene, 2,4,6-trimethylstyrene, and the like. . These may be used alone or in combination of two or more. Among these, styrene is particularly preferable from the viewpoint of practical use such as availability of monomers.
前記一般式で表される窒素含有化合物としては、例えば3−または4−(2−アゼチジノエチル)スチレン、3−または4−(2−ピロリジノエチル)スチレン、3−または4−(2−ピペリジノエチル)スチレン、3−または4−(2−ヘキサメチレンイミノエチル)スチレン、3−または4−(2−ヘプタメチレンイミノエチル)スチレン、3−または4−(2−オクタメチレンイミノエチル)スチレン、3−または4−(2−(2,5−ジメチルピロリジノ)エチル)スチレン、3−または4−(2−(2−メチルピペリジノ)エチル)スチレン、3−または4−(2−(3−メチルピペリジノ)エチル)スチレン、3−または4−(2−(4−メチルピペリジノ)エチル)スチレン、3−または4−(2−(2−エチルピペリジノ)エチル)スチレン、3−または4−(2−(4−(1−ピロリジニル)ピペリジノ)エチル)スチレン、3−または4−(2−(4−ピペリジノピペリジノ)エチル)スチレン、3−または4−(2−(2,6−ジメチルピペリジノ)エチル)スチレン、3−または4−(2−(3,3−ジメチルピペリジノ)エチル)スチレン、3−または4−(2−(3,5−ジメチルピペリジノ)エチル)スチレン、3−または4−(2−(2,2,6,6−テトラメチルピペリジノ)エチル)スチレン、3−または4−(2−(4−ジメチルアミノ−2,2,6,6−テトラメチルピペリジノ)エチル)スチレン、3−または4−(2−(1−メチルピペラジノ)エチル)スチレン、3−または4−(2−(1−エチルピペラジノ)エチル)スチレン、3−または4−(2−(1−メチルホモピペラジノ)エチル)スチレン、3−または4−(2−モルホリノエチル)スチレン、3−または4−(2−(2,6−ジメチルモルホリノ)エチル)スチレン、3−または4−(2−チアゾリジノエチル)スチレン、3−または4−(2−トオモルホリノエチル)スチレン、3−または4−(2−ジメチルアミノエチル)スチレン、3−または4−(2−(N−エチルメチルアミノ)エチル)スチレン、3−または4−(2−ジエチルアミノエチル)スチレン、3−または4−(2−(N−メチルプロピルアミノ)エチル)スチレン、3−または4−(2−(N−メチルイソプロピルアミノ)エチル)スチレン、3−または4−(2−(N−エチルイソプロピルアミノ)エチル)スチレン、3−または4−(2−ジプロピルアミノエチル)スチレン、3−または4−(2−ジイソプロピルアミノエチル)スチレン、3−または4−(2−(N−メチルブチルアミノ)エチル)スチレン、3−または4−(2−(N−エチルブチルアミノ)エチル)スチレン、3−または4−(2−(N−メチル−tert−ブチルアミノ)エチル)スチレン、3−または4−(2−(N−tert−ブチルイソプロピルアミノ)エチル)スチレン、3−または4−(2−ジブチルアミノエチル)スチレン、3−または4−(2−ジ−sec−ブチルアミノエチル)スチレン、3−または4−(2−ジイソブチルアミノエチル)スチレン、3−または4−(2−(tert−アミル−tert−ブチルアミノ)エチル)スチレン、3−または4−(2−ジペンチルアミノエチル)スチレン、3−または4−(2−(N−メチルヘキシルアミノ)エチル)スチレン、3−または4−(2−ジヘキシルアミノエチル)スチレン、3−または4−(2−(tert−アミル−tert−オクチルアミノ)エチル)スチレン、3−または4−(2−ジオクチルアミノエチル)スチレン、3−または4−(2−ビス(2−エチルヘキシルアミノ)エチル)スチレン、3−または4−(2−ジデシルアミノエチル)スチレン、3−または4−(2−(N−メチルオクタデシルアミノ)エチル)スチレン、3−または4−(2−(N−メチルアニリノ)エチル)スチレン、3−または4−(2−ジフェニルアミノエチル)スチレン、3−または4−(2−(N−フェニルベンジルアミノ)エチル)スチレン、3−または4−(2−(N−フェニル−1−ナフチルアミノ)エチル)スチレン、3−または4−(2−(N−フェニル−2−ナフチルアミノ)エチル)スチレン、3−または4−(2−(N−ベンジルメチルアミノ)エチル)スチレン、3−または4−(2−(N−エチルベンジルアミノ)エチル)スチレン、3−または4−(2−(N−イソプロピルベンジルアミノ)エチル)スチレン、3−または4−(2−(N−ブチルベンジルアミノ)エチル)スチレン、3−または4−(2−(N−(tert−ブチル)ベンジルアミノ)エチル)スチレン、3−または4−(2−ジベンジルアミノエチル)スチレン、3−または4−(2−(N−メチルフェネチルアミノ)エチル)スチレン、3−または4−(2−(N−ベンジル−2−フェネチルアミノ)エチル)スチレン、3−または4−(2−(4−ベンジルピペリジノ)エチル)スチレン、3−または4−(2−(1−フェニルピペラジノ)エチル)スチレン、3−または4−(2−(1−ベンジルピペラジノ)エチル)スチレン、3−または4−(2−インドリノエチル)スチレン、3−または4−(2−(2−メチルインドリノ)エチル)スチレン、3−または4−(2−(1,2,3,4−テトラヒドロキノリノ)エチル)スチレン、3−または4−(2−(1,2,3,4−テトラヒドロイソキノリノ)エチル)スチレン、3−または4−(2−フェノキサジノエチル)スチレン、3−または4−(2−フェノチアジノエチル)スチレン、3−または4−(2−アニリノピリジノエチル)スチレン、3−または4−(2−(2−ベンジルアミノピリジノ)エチル)スチレン、3−または4−(2−(2,2’−ジピリジルアミノ)エチル)スチレン、3−または4−(2−(2−メチルアミノ)ピリジノエチル)スチレン、3−または4−(2−(1−(2−ピリジル)ピペラジノ)エチル)スチレン、3−または4−(2−(2−(2−メチルアミノエチル)ピリジノ)エチル)スチレン、3−または4−(2−(4−(エチルアミノメチル)ピリジノ)エチル)スチレン、3−または4−(2−(4−(エチルアミノメチル)ピリジノ)エチル)スチレンなどがあげられる。これらは単独で用いても良いし、2種以上を組み合わせて用いても良い。これらの中では、性能改善の効果の点で、3−または4−(2−ジメチルアミノエチル)スチレン、3−または4−(2−ピロリジノエチル)スチレン、3−または4−(2−ピペリジノエチル)スチレン、3−または4−(2−ヘキサメチレンイミノエチル)スチレン、3−または4−(2−モルホリノエチル)スチレン、及び、3−または4−(2−チアゾリジノエチル)スチレンが好ましい。 Examples of the nitrogen-containing compound represented by the general formula include 3- or 4- (2-azetidinoethyl) styrene, 3- or 4- (2-pyrrolidinoethyl) styrene, 3- or 4- (2-piperidinoethyl). Styrene, 3- or 4- (2-hexamethyleneiminoethyl) styrene, 3- or 4- (2-heptamethyleneiminoethyl) styrene, 3- or 4- (2-octamethyleneiminoethyl) styrene, 3- or 4- (2- (2,5-dimethylpyrrolidino) ethyl) styrene, 3- or 4- (2- (2-methylpiperidino) ethyl) styrene, 3- or 4- (2- (3-methylpiperidino) ethyl) Styrene, 3- or 4- (2- (4-methylpiperidino) ethyl) styrene, 3- or 4- (2- (2-ethylpiperidino) Chill) styrene, 3- or 4- (2- (4- (1-pyrrolidinyl) piperidino) ethyl) styrene, 3- or 4- (2- (4-piperidinopiperidino) ethyl) styrene, 3- Or 4- (2- (2,6-dimethylpiperidino) ethyl) styrene, 3- or 4- (2- (3,3-dimethylpiperidino) ethyl) styrene, 3- or 4- (2- (3,5-dimethylpiperidino) ethyl) styrene, 3- or 4- (2- (2,2,6,6-tetramethylpiperidino) ethyl) styrene, 3- or 4- (2- ( 4-dimethylamino-2,2,6,6-tetramethylpiperidino) ethyl) styrene, 3- or 4- (2- (1-methylpiperazino) ethyl) styrene, 3- or 4- (2- (1 -Ethylpiperazino) ethyl) styrene 3- or 4- (2- (1-methylhomopiperazino) ethyl) styrene, 3- or 4- (2-morpholinoethyl) styrene, 3- or 4- (2- (2,6-dimethylmorpholino) Ethyl) styrene, 3- or 4- (2-thiazolidinoethyl) styrene, 3- or 4- (2-tomorpholinoethyl) styrene, 3- or 4- (2-dimethylaminoethyl) styrene, 3- or 4- (2- (N-ethylmethylamino) ethyl) styrene, 3- or 4- (2-diethylaminoethyl) styrene, 3- or 4- (2- (N-methylpropylamino) ethyl) styrene, 3- Or 4- (2- (N-methylisopropylamino) ethyl) styrene, 3- or 4- (2- (N-ethylisopropylamino) ethyl) styrene, 3- or Is 4- (2-dipropylaminoethyl) styrene, 3- or 4- (2-diisopropylaminoethyl) styrene, 3- or 4- (2- (N-methylbutylamino) ethyl) styrene, 3- or 4 -(2- (N-ethylbutylamino) ethyl) styrene, 3- or 4- (2- (N-methyl-tert-butylamino) ethyl) styrene, 3- or 4- (2- (N-tert- Butylisopropylamino) ethyl) styrene, 3- or 4- (2-dibutylaminoethyl) styrene, 3- or 4- (2-di-sec-butylaminoethyl) styrene, 3- or 4- (2-diisobutylamino) Ethyl) styrene, 3- or 4- (2- (tert-amyl-tert-butylamino) ethyl) styrene, 3- or 4- (2-dipene) Ruaminoethyl) styrene, 3- or 4- (2- (N-methylhexylamino) ethyl) styrene, 3- or 4- (2-dihexylaminoethyl) styrene, 3- or 4- (2- (tert-amyl- tert-octylamino) ethyl) styrene, 3- or 4- (2-dioctylaminoethyl) styrene, 3- or 4- (2-bis (2-ethylhexylamino) ethyl) styrene, 3- or 4- (2- Didecylaminoethyl) styrene, 3- or 4- (2- (N-methyloctadecylamino) ethyl) styrene, 3- or 4- (2- (N-methylanilino) ethyl) styrene, 3- or 4- (2 -Diphenylaminoethyl) styrene, 3- or 4- (2- (N-phenylbenzylamino) ethyl) styrene, 3-methyl Is 4- (2- (N-phenyl-1-naphthylamino) ethyl) styrene, 3- or 4- (2- (N-phenyl-2-naphthylamino) ethyl) styrene, 3- or 4- (2- (N-benzylmethylamino) ethyl) styrene, 3- or 4- (2- (N-ethylbenzylamino) ethyl) styrene, 3- or 4- (2- (N-isopropylbenzylamino) ethyl) styrene, 3 -Or 4- (2- (N-butylbenzylamino) ethyl) styrene, 3- or 4- (2- (N- (tert-butyl) benzylamino) ethyl) styrene, 3- or 4- (2-di Benzylaminoethyl) styrene, 3- or 4- (2- (N-methylphenethylamino) ethyl) styrene, 3- or 4- (2- (N-benzyl-2-phenethylamino) 6) ethyl) styrene, 3- or 4- (2- (4-benzylpiperidino) ethyl) styrene, 3- or 4- (2- (1-phenylpiperazino) ethyl) styrene, 3- or 4 -(2- (1-benzylpiperazino) ethyl) styrene, 3- or 4- (2-indolinoethyl) styrene, 3- or 4- (2- (2-methylindolino) ethyl) styrene, 3 -Or 4- (2- (1,2,3,4-tetrahydroquinolino) ethyl) styrene, 3- or 4- (2- (1,2,3,4-tetrahydroisoquinolino) ethyl) styrene, 3- or 4- (2-phenoxazinoethyl) styrene, 3- or 4- (2-phenothiazinoethyl) styrene, 3- or 4- (2-anilinopyridinoethyl) styrene, 3- or 4 -(2- (2 Benzylaminopyridino) ethyl) styrene, 3- or 4- (2- (2,2′-dipyridylamino) ethyl) styrene, 3- or 4- (2- (2-methylamino) pyridinoethyl) styrene, 3- Or 4- (2- (1- (2-pyridyl) piperazino) ethyl) styrene, 3- or 4- (2- (2- (2-methylaminoethyl) pyridino) ethyl) styrene, 3- or 4- ( 2- (4- (ethylaminomethyl) pyridino) ethyl) styrene, 3- or 4- (2- (4- (ethylaminomethyl) pyridino) ethyl) styrene and the like can be mentioned. These may be used alone or in combination of two or more. Of these, 3- or 4- (2-dimethylaminoethyl) styrene, 3- or 4- (2-pyrrolidinoethyl) styrene, 3- or 4- (2-piperidinoethyl) is effective in improving performance. Styrene, 3- or 4- (2-hexamethyleneiminoethyl) styrene, 3- or 4- (2-morpholinoethyl) styrene and 3- or 4- (2-thiazolidinoethyl) styrene are preferred.
前記重合体は、前記窒素含有化合物を、共役ジエン化合物および/または芳香族ビニル化合物と共重合させることにより製造する。重合方法については特に制限はなく、溶液重合法、気相重合法、バルク重合法のいずれも用いることができるが、特に重合体の設計の自由度、加工性等の観点から溶液重合法が好ましい。また、重合形式は、回分式及び連続式のいずれであってもよい。 The polymer is produced by copolymerizing the nitrogen-containing compound with a conjugated diene compound and / or an aromatic vinyl compound. The polymerization method is not particularly limited, and any of solution polymerization method, gas phase polymerization method, and bulk polymerization method can be used. In particular, the solution polymerization method is preferable from the viewpoint of the degree of freedom in polymer design, processability, and the like. . Moreover, any of a batch type and a continuous type may be sufficient as the superposition | polymerization form.
溶液重合法においては、例えばリチウム化合物を重合開始剤とし、窒素含有化合物を、共役ジエン化合物および/または芳香族ビニル化合物をアニオン重合させることにより、目的の重合体を製造することができる。溶液重合法を用いた場合には、溶媒中のモノマー濃度は、5質量%以上が好ましく、10質量%以上がより好ましい。溶液中のモノマー濃度が5質量%未満では、得られる重合体の量が少なく、コストが高くなる傾向がある。また、溶媒中のモノマー濃度は50質量%以下が好ましく、30質量%以下がより好ましい。溶媒中のモノマー濃度が50質量%をこえると、溶液粘度が高くなりすぎて撹拌が困難となり、重合しにくくなる傾向がある。 In the solution polymerization method, for example, a target polymer can be produced by anionic polymerization of a nitrogen-containing compound and a conjugated diene compound and / or an aromatic vinyl compound using a lithium compound as a polymerization initiator. When the solution polymerization method is used, the monomer concentration in the solvent is preferably 5% by mass or more, and more preferably 10% by mass or more. When the monomer concentration in the solution is less than 5% by mass, the amount of the obtained polymer is small and the cost tends to be high. The monomer concentration in the solvent is preferably 50% by mass or less, and more preferably 30% by mass or less. When the monomer concentration in the solvent exceeds 50% by mass, the solution viscosity becomes too high, stirring becomes difficult, and polymerization tends to be difficult.
アニオン重合を行う場合、重合開始剤としては特に制限はないが、有機リチウム化合物が好ましく用いられる。前記有機リチウム化合物としては、炭素数2〜20のアルキル基を有するものが好ましく、例えばエチルリチウム、n−プロピルリチウム、イソプロピルリチウム、n−ブチルリチウム、sec−ブチルリチウム、tert−ブチルリチウム、tert−オクチルリチウム、n−デシルリチウム、フェニルリチウム、2−ナフチルリチウム、2−ブチルーフェニルリチウム、4−フェニル−ブチルリチウム、シクロヘキシルリチウム、シクロペンチルリチウム、ジイソプロペニルベンゼンとブチルリチウムとの反応生成物などが挙げられるが、これらの中で、入手容易性、安全性等の観点からn−ブチルリチウムまたはsec−ブチルリチウムが好ましい。 When anionic polymerization is performed, the polymerization initiator is not particularly limited, but an organic lithium compound is preferably used. As the organic lithium compound, those having an alkyl group having 2 to 20 carbon atoms are preferable. For example, ethyl lithium, n-propyl lithium, isopropyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium, tert- Octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2-butyl-phenyl lithium, 4-phenyl-butyl lithium, cyclohexyl lithium, cyclopentyl lithium, reaction products of diisopropenylbenzene and butyl lithium, etc. Among these, n-butyllithium or sec-butyllithium is preferable from the viewpoints of availability, safety, and the like.
前記有機リチウム化合物を重合開始剤として用い、アニオン重合によって重合体を製造する方法としては、特に制限はなく、従来公知の方法を用いることができる。具体的には、反応に不活性な有機溶剤、例えば脂肪族、脂環族、芳香族炭化水素化合物などの炭化水素系溶剤中において、共役ジエン化合物および/または芳香族ビニル化合物と一般式で表される窒素含有化合物を、前記リチウム化合物を重合開始剤として、必要に応じてランダマイザーの存在下でアニオン重合させることにより、目的の重合体が得られる。 There is no restriction | limiting in particular as a method of manufacturing a polymer by anionic polymerization using the said organic lithium compound as a polymerization initiator, A conventionally well-known method can be used. Specifically, in an organic solvent inert to the reaction, for example, a hydrocarbon solvent such as an aliphatic, alicyclic, and aromatic hydrocarbon compound, the conjugated diene compound and / or the aromatic vinyl compound is represented by the general formula. The target polymer is obtained by subjecting the nitrogen-containing compound to anionic polymerization in the presence of a randomizer, if necessary, using the lithium compound as a polymerization initiator.
前記炭化水素系溶剤としては、炭素数3〜8のものが好ましく、例えばプロパン、n−ブタン、イソブタン、n−ペンタン、イソペンタン、n−ヘキサン、シクロヘキサン、プロペン、1−ブテン、イソブテン、トランス−2−ブテン、シス−2−ブテン、1−ペンテン、2−ペンテン、1−ヘキセン、2−ヘキセン、ベンゼン、トルエン、キシレン、エチルベンゼンなどを挙げることができる。これらは単独で用いてもよく、2種以上を混合して用いてもよい。 The hydrocarbon solvent is preferably one having 3 to 8 carbon atoms, such as propane, n-butane, isobutane, n-pentane, isopentane, n-hexane, cyclohexane, propene, 1-butene, isobutene and trans-2. -Butene, cis-2-butene, 1-pentene, 2-pentene, 1-hexene, 2-hexene, benzene, toluene, xylene, ethylbenzene and the like. These may be used alone or in combination of two or more.
また、前記ランダマイザーとは、重合体中の共役ジエン部分のミクロ構造制御、例えばブタジエンにおける1、2−結合、イソプレンにおける3、4−結合の増加など、あるいは重合体におけるモノマー単位の組成分布の制御、例えばブタジエン−スチレン共重合体におけるブタジエン単位、スチレン単位のランダム化などの作用を有する化合物のことである。このランダマイザーとしては、特に制限はなく、従来ランダマイザーとして一般に使用されている公知の化合物の中から任意のものを用いることができる。例えば、ジメトキシベンゼン、テトラヒドロフラン、ジメトキシエタン、ジエチレングリコールジブチルエーテル、ジエチレングリコールジメチルエーテル、ビステトラヒドロフリルプロパン、トリエチルアミン、ピリジン、N−メチルモルホリン、N,N,N’,N’−テトラメチルエチレンジアミン、1,2−ジピペリジノエタンなどのエーテル類及び第三級アミン類などを挙げることができる。また、カリウム−t−アミレート、カリウム−t−ブトキシドなどのカリウム塩類、ナトリウム−t−アミレートなどのナトリウム塩類も用いることができる。これらのランダマイザーは、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。また、ランダマイザーの使用量は、有機リチウム化合物1モル当たり、0.01モル当量以上が好ましく、0.05モル当量以上がより好ましい。ランダマイザーの使用量が0.01モル当量未満では、添加効果が小さく、ランダム化しにくい傾向がある。また、ランダマイザーの使用量は、有機リチウム化合物1モル当たり1000モル当量以下が好ましく、500モル当量以下がより好ましい。ランダマイザーの使用量が1000モル当量をこえると、モノマーの反応速度が大きく変化してしまい、逆にランダム化しにくくなる傾向がある。 The randomizer is a microstructure control of a conjugated diene moiety in a polymer, for example, an increase in 1,2-bond in butadiene, an increase in 3,4-bond in isoprene, or a composition distribution of monomer units in the polymer. It is a compound having control, for example, randomization of butadiene units and styrene units in a butadiene-styrene copolymer. The randomizer is not particularly limited, and any known compound generally used as a conventional randomizer can be used. For example, dimethoxybenzene, tetrahydrofuran, dimethoxyethane, diethylene glycol dibutyl ether, diethylene glycol dimethyl ether, bistetrahydrofurylpropane, triethylamine, pyridine, N-methylmorpholine, N, N, N ′, N′-tetramethylethylenediamine, 1,2-di Examples include ethers such as piperidinoethane and tertiary amines. Further, potassium salts such as potassium-t-amylate and potassium-t-butoxide, and sodium salts such as sodium-t-amylate can also be used. These randomizers may be used individually by 1 type, and may be used in combination of 2 or more type. The amount of randomizer used is preferably 0.01 molar equivalents or more, more preferably 0.05 molar equivalents or more per mole of the organic lithium compound. If the amount of randomizer used is less than 0.01 molar equivalent, the effect of addition tends to be small and it tends to be difficult to randomize. The amount of randomizer used is preferably 1000 molar equivalents or less, more preferably 500 molar equivalents or less, per mole of the organic lithium compound. If the amount of randomizer used exceeds 1000 molar equivalents, the reaction rate of the monomer changes greatly, and conversely, it tends to be difficult to randomize.
前記重合体は、少なくとも一方の末端が窒素、酸素、ケイ素の中から選ばれる少なくとも一つの原子を含む官能基を有する変性剤で変性されていてもよい。窒素、酸素、ケイ素の中から選ばれる少なくとも1つの原子を含む官能基としては、例えばアミノ基、アミド基、アルコキシシリル基、イソシアネート基、イミノ基、イミダゾール基、ウレア基、エーテル基、カルボニル基、カルボキシル基、ヒドロキシル基、ニトリル基、ピリジル基等があげられる。変性剤としては、例えば3−グリシドキシプロピルトリメトキシシラン、(3−トリエトキシシリルプロピル)テトラスルフィド、1−(4−N,N−ジメチルアミノフェニル)−1−フェニルエチレン、1,1−ジメトキシトリメチルアミン、1,2−ビス(トリクロロシリル)エタン、1,3,5−トリス(3−トリエトキシシリルプロピル)イソシアヌレート、1,3,5−トリス(3−トリメトキシシリルプロピル)イソシアヌレート、1,3−ジメチル−2−イミダゾリジノン、1,3−プロパンジアミン、1,4−ジアミノブタン、1−[3−(トリエトキシシリル)プロピル]−4,5−ジヒドロイミダゾール、1−グリシジル−4−(2−ピリジル)ピペラジン、1−グリシジル−4−フェニルピペラジン、1−グリシジル−4−メチルピペラジン、1−グリシジル−4−メチルホモピペラジン、1−グリシジルヘキサメチレンイミン、11−アミノウンデシルトリエトキシシラン、11−アミノウンデシルトリメトキシシラン、1−ベンジル−4−グリシジルピペラジン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、2−(4−モルフォリノジチオ)ベンゾチアゾール、2−(6−アミノエチル)−3−アミノプロピルトリメトキシシラン、2−(トリエトキシシリルエチル)ピリジン、2−(トリメトキシシリルエチル)ピリジン、2−(2−ピリジルエチル)チオプロピルトリメトキシシラン、2−(4−ピリジルエチル)チオプロピルトリメトキシシラン、2,2−ジエトキシ−1,6−ジアザ−2−シラシクロオクタン、2,2−ジメトキシ−1,6−ジアザ−2−シラシクロオクタン、2,3−ジクロロ−1,4−ナフトキノン、2,4−ジニトロベンゼンスルホニルクロライド、2,4−トリレンジイソシアナート、2−(4−ピリジルエチル)トリエトキシシラン、2−(4−ピリジルエチル)トリメトキシシラン、2−シアノエチルトリエトキシシラン、2−トリブチルスタニル−1,3−ブタジエン、2−(トリメトキシシリルエチル)ピリジン、2−ビニルピリジン、2−(4−ピリジルエチル)トリエトキシシラン、2−(4−ピリジルエチル)トリメトキシシラン、2−ラウリルチオエチルフェニルケトン、3−(1−ヘキサメチレンイミノ)プロピル(トリエトキシ)シラン、3−(1,3−ジメチルブチリデン)アミノプロピルトリエトキシシラン、3−(1,3−ジメチルブチリデン)アミノプロピルトリメトキシシラン、3−(2−アミノエチルアミノプロピル)トリメトキシシラン、3−(m−アミノフェノキシ)プロピルトリメトキシシラン、3−(N,N−ジメチルアミノ)プロピルトリエトキシシラン、3−(N,N−ジメチルアミノ)プロピルトリメトキシシラン、3−(N−メチルアミノ)プロピルトリエトキシシラン、3−(N−メチルアミノ)プロピルトリメトキシシラン、3−(N−アリルアミノ)プロピルトリメトキシシラン、3,4−ジアミノ安息香酸、3−アミノプロピルジメチルエトキシシラン、3−アミノプロピルトリエトキシシラン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリス(メトキシジエトキシ)シラン、3−アミノプロピルジイソプロピルエトキシシラン、3−イソシアネートプロピルトリエトキシシラン、3−グリシドキシプロピルトリエトキシシラン、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン、3−ジエチルアミノプロピルトリメトキシシラン、3−ジエトキシ(メチル)シリルプロピル無水コハク酸、3−(N,N−ジエチルアミノプロピル)トリエトキシシラン、3−(N,N−ジエチルアミノプロピル)トリメトキシシラン、3−(N,N−ジメチルアミノプロピル)ジエトキシメチルシラン、3−(N,N−ジメチルアミノプロピル)トリエトキシシラン、3−(N,N−ジメチルアミノプロピル)トリメトキシシラン、3−トリエトキシシリルプロピル無水コハク酸、3−トリエトキシシリルプロピル無水酢酸、3−トリフェノキシシリルプロピル無水コハク酸、3−トリフェノキシシリルプロピル無水酢酸、3−トリメトキシシリルプロピルベンゾチアゾールテトラスルフィド、3−ヘキサメチレンイミノプロピルトリエトキシシラン、3−メルカプトプロピルトリメトキシシラン、(3−トリエトキシシリルプロピル)ジエチレントリアミン、(3−トリメトキシシリルプロピル)ジエチレントリアミン、4,4’−ビス(ジエチルアミノ)ベンゾフェノン、4,4’−ビス(ジメチルアミノ)ベンゾフェノン、4’−(イミダゾール−1−イル)−アセトフェノン、4−〔3−(N,N−ジグリシジルアミノ)プロピル〕モルホリン、4−グリシジル−2,2,6,6−テトラメチルピペリジニルオキシ、4−アミノブチルトリエトキシシラン、4−ビニルピリジン、4−モルホリノアセトフェノン、4−モルホリノベンゾフェノン、m−アミノフェニルトリメトキシシラン、N−(1,3−ジメチルブチリデン)−3−(トリエトキシシリル)−1−プロパンアミン、N−(1,3−ジメチルブチリデン)−3−(トリメトキシシリル)−1−プロパンアミン、N−(1−メチルエチリデン)−3−(トリエトキシシリル)−1−プロパンアミン、N−(2−アミノエチル)−3−アミノプロピルメチルジエトキシシラン、N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリエトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、N−(2−アミノエチル)−11−アミノウンデシルトリエトキシシラン、N−(2−アミノエチル)−11−アミノウンデシルトリメトキシシラン、N−(2−アミノエチル)−3−アミノイソブチルメチルジエトキシシラン、N−(2−アミノエチル)−3−アミノイソブチルメチルジメトキシシラン、N−(3−ジエトキシメチルシリルプロピル)サクシンイミド、N−(3−トリエトキシシリルプロピル)−4,5−ジヒドロイミダゾール、N−(3−トリエトキシシリルプロピル)ピロール、N−(3−トリメトキシシリルプロピル)ピロール、N−3−[アミノ(ポリプロピレンオキシ)]アミノプロピルトリメトキシシラン、N−[5−(トリエトキシシリル)−2−アザー1−オキソペンチル]カプロラクタム、N−[5−(トリメトキシシリル)−2−アザー1−オキソペンチル]カプロラクタム、N−(6−アミノヘキシル)アミノメチルトリエトキシシラン、N−(6−アミノヘキシル)アミノメチルトリメトキシシラン、N−アリル−アザ−2,2−ジエトキシシラシクロペンタン、N−アリル−アザ−2,2−ジメトキシシラシクロペンタン、N−(シクロヘキシルチオ)フタルイミド、N−n−ブチル−アザ−2,2−ジエトキシシラシクロペンタン、N−n−ブチル−アザ−2,2−ジメトキシシラシクロペンタン、N,N,N’,N’−テトラエチルアミノベンゾフェノン、N,N,N’,N’−テトラメチルチオ尿素、N,N,N’,N’−テトラメチル尿素、N,N’−エチレン尿素、N,N’−ジエチルアミノベンゾフェノン、N,N’−ジエチルアミノベンゾフェノン、N,N’−ジエチルアミノベンゾフラン、N,N’−ジエチルカルバミン酸メチル、N,N’−ジエチル尿素、(N,N−ジエチル−3−アミノプロピル)トリエトキシシラン、(N,N−ジエチル−3−アミノプロピル)トリメトキシシラン、N,N−ジオクチル−N’−トリエトキシシリルプロピルウレア、N,N−ジオクチル−N’−トリメトキシシリルプロピルウレア、N,N−ジエチルカルバミン酸メチル、N,N−ジグリシジルシクロヘキシルアミン、N,N−ジメチル−o−トルイジン、N,N−ジメチルアミノスチレン、N,N−ジエチルアミノプロピルアクリルアミド、N,N−ジメチルアミノプロピルアクリルアミド、N−エチルアミノイソブチルトリエトキシシラン、N−エチルアミノイソブチルトリメトキシシラン、N−エチルアミノイソブチルメチルジエトキシシラン、N−オキシジエチレン−2−ベンゾチアゾールスルフェンアミド、N−シクロヘキシルアミノプロピルトリエトキシシラン、N−シクロヘキシルアミノプロピルトリメトキシシラン、N−メチルアミノプロピルメチルジメトキシシラン、N−メチルアミノプロピルメチルジエトキシシラン、N−ビニルベンジルアザシクロヘプタン、N−フェニルピロリドン、N−フェニルアミノプロピルトリエトキシシラン、N−フェニルアミノプロピルトリメトキシシラン、N−フェニルアミノメチルトリエトキシシラン、N−フェニルアミノメチルトリメトキシシラン、n−ブチルアミノプロピルトリエトキシシラン、n−ブチルアミノプロピルトリメトキシシラン、N−メチルアミノプロピルトリエトキシシラン、N−メチルアミノプロピルトリメトキシシラン、N−メチル−2−ピペリドン、N−メチル−2−ピロリドン、N−メチル−ε−カプロラクタム、N−メチルインドリノン、N−メチルピロリドン、p−(2−ジメチルアミノエチル)スチレン、p−アミノフェニルトリメトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−メタクリロキシプロピルトリメトキシシラン、(アミノエチルアミノ)−3−イソブチルジエトキシシラン、(アミノエチルアミノ)−3−イソブチルジメトキシシラン、(アミノエチルアミノメチル)フェネチルトリエトキシシラン、(アミノエチルアミノメチル)フェネチルトリメトキシシラン、アクリル酸、アジピン酸ジエチル、アセタミドプロピルトリメトキシシラン、アミノフェニルトリメトキシシラン、アミノベンゾフェノン、ウレイドプロピルトリエトキシシラン、ウレイドプロピルトリメトキシシラン、エチレンオキシド、オクタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロリド、グリシドキシプロピルトリエトキシシラン、グリシドキシプロピルトリメトキシシラン、グリセロールトリステアレート、クロロトリエトキシシラン、クロロプロピルトリエトキシシラン、クロロポリジメチルシロキサン、クロロメチルジフェノキシシラン、ジアリルジフェニルスズ、ジエチルアミノメチルトリエトキシシラン、ジエチルアミノメチルトリメトキシシラン、ジエチル(グリシジル)アミン、ジエチルジチオカルバミン酸2−ベンゾチアゾイルエステル、ジエトキシジクロロシラン、(シクロヘキシルアミノメチル)トリエトキシシラン、(シクロヘキシルアミノメチル)トリメトキシシラン、ジグリシジルポリシロキサン、ジクロロジフェノキシシラン、ジシクロヘキシルカルボジイミド、ジビニルベンゼン、ジフェニルカルボジイミド、ジフエニルシアナミド、ジフェニルメタンジイソシアネート、ジフェノキシメチルクロロシラン、ジブチルジクロロスズ、ジメチル(アセトキシ−メチルシロキサン)ポリジメチルシロキサン、ジメチルアミノメチルトリエトキシシラン、ジメチルアミノメチルトリメトキシシラン、ジメチル(メトキシ−メチルシロキサン)ポリジメチルシロキサン、ジメチルイミダゾリジノン、ジメチルエチレン尿素、ジメチルジクロロシラン、ジメチルスルホモイルクロライド、シルセスキオキサン、ソルビタントリオレイン酸エステル、ソルビタンモノラウリン酸エステル、チタンテトラキス(2−エチルヘキシオキシド)、テトラエトキシシラン、テトラグリシジル−1,3−ビスアミノメチルシクロヘキサン、テトラフェノキシシラン、テトラメチルチウラムジスルフィド、テトラメトキシシラン、トリエトキシビニルシラン、トリス(3−トリメトキシシリルプロピル)シアヌレート、トリフェニルホスフェート、トリフェノキシクロロシラン、トリフェノキシメチルケイ素、トリフェノキシメチルシラン、二酸化
炭素、ビス(トリエトキシシリルプロピル)アミン、ビス(トリメトキシシリルプロピル)アミン、ビス[3−(トリエトキシシリル)プロピル]エチレンジアミン、ビス[3−(トリメトキシシリル)プロピル]エチレンジアミン、ビス[3−(トリエトキシシリル)プロピル]ウレア、ビス[(トリメトキシシリル)プロピル]ウレア、ビス(2−ヒドロキシメチル)−3−アミノプロピルトリエトキシシラン、ビス(2−ヒドロキシメチル)−3−アミノプロピルトリメトキシシラン、ビス(2−エチルヘキサノエート)スズ、ビス(2−メチルブトキシ)メチルクロロシラン、ビス(3−トリエトキシシリルプロピル)テトラスルフィド、ビスジエチルアミノベンゾフェノン、ビスフェノールAジグリシジルエーテル、ビスフェノキシエタノールフルオレンジグリシジルエーテル、ビス(メチルジエトキシシリルプロピル)アミン、ビス(メチルジメトキシシリルプロピル)−N−メチルアミン、ヒドロキシメチルトリエトキシシラン、ビニルトリス(2−エチルヘキシルオキシ)シラン、ビニルベンジルジエチルアミン、ビニルベンジルジメチルアミン、ビニルベンジルトリブチルスズ、ビニルベンジルピペリジン、ビニルベンジルピロリジン、ピロリジン、フェニルイソシアナート、フェニルイソチオシアナート、(フェニルアミノメチル)メチルジメトキシシラン、(フェニルアミノメチル)メチルジエトキシシラン、フタル酸アミド、ヘキサメチレンジイソシアナート、ベンジリデンアニリン、ポリジフェニルメタンジイソシアネート、ポリジメチルシロキサン、メチル−4−ピリジルケトン、メチルカプロラクタム、メチルトリエトキシシラン、メチルトリフェノキシシラン、ラウリルチオプロピオン酸メチル、四塩化ケイ素等があげられる。これらの中では、性能改善の効果の点で、3−(N,N−ジメチルアミノプロピル)トリメトキシシラン、3−(N,N−ジエチルアミノプロピル)トリメトキシシラン、3−(N,N−ジメチルアミノプロピル)トリエトキシシラン、3−(N,N−ジエチルアミノプロピル)トリエトキシシラン、3−グリシドキシプロピルトリメトキシシラン、2−(4−ピリジルエチル)トリエトキシシラン、N−(3−トリエトキシシリルプロピル)−4,5−ジヒドロイミダゾール、四塩化ケイ素等が好ましい。
The polymer may be modified with a modifier having a functional group containing at least one atom selected from nitrogen, oxygen, and silicon at least one terminal. Examples of the functional group containing at least one atom selected from nitrogen, oxygen, and silicon include an amino group, an amide group, an alkoxysilyl group, an isocyanate group, an imino group, an imidazole group, a urea group, an ether group, a carbonyl group, Examples thereof include a carboxyl group, a hydroxyl group, a nitrile group, and a pyridyl group. Examples of the modifier include 3-glycidoxypropyltrimethoxysilane, (3-triethoxysilylpropyl) tetrasulfide, 1- (4-N, N-dimethylaminophenyl) -1-phenylethylene, 1,1- Dimethoxytrimethylamine, 1,2-bis (trichlorosilyl) ethane, 1,3,5-tris (3-triethoxysilylpropyl) isocyanurate, 1,3,5-tris (3-trimethoxysilylpropyl) isocyanurate, 1,3-dimethyl-2-imidazolidinone, 1,3-propanediamine, 1,4-diaminobutane, 1- [3- (triethoxysilyl) propyl] -4,5-dihydroimidazole, 1-glycidyl- 4- (2-pyridyl) piperazine, 1-glycidyl-4-phenylpiperazine, 1-glycidyl 4-methylpiperazine, 1-glycidyl-4-methylhomopiperazine, 1-glycidylhexamethyleneimine, 11-aminoundecyltriethoxysilane, 11-aminoundecyltrimethoxysilane, 1-benzyl-4-glycidylpiperazine, 2 -(3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (4-morpholinodithio) benzothiazole, 2- (6-aminoethyl) -3-aminopropyltrimethoxysilane, 2- (triethoxysilylethyl) ) Pyridine, 2- (trimethoxysilylethyl) pyridine, 2- (2-pyridylethyl) thiopropyltrimethoxysilane, 2- (4-pyridylethyl) thiopropyltrimethoxysilane, 2,2-diethoxy-1,6 -Diaza-2-silacyclooctane, 2, -Dimethoxy-1,6-diaza-2-silacyclooctane, 2,3-dichloro-1,4-naphthoquinone, 2,4-dinitrobenzenesulfonyl chloride, 2,4-tolylene diisocyanate, 2- (4- Pyridylethyl) triethoxysilane, 2- (4-pyridylethyl) trimethoxysilane, 2-cyanoethyltriethoxysilane, 2-tributylstannyl-1,3-butadiene, 2- (trimethoxysilylethyl) pyridine, 2- Vinylpyridine, 2- (4-pyridylethyl) triethoxysilane, 2- (4-pyridylethyl) trimethoxysilane, 2-laurylthioethylphenylketone, 3- (1-hexamethyleneimino) propyl (triethoxy) silane, 3- (1,3-Dimethylbutylidene) aminopropyltriethoxysila 3- (1,3-dimethylbutylidene) aminopropyltrimethoxysilane, 3- (2-aminoethylaminopropyl) trimethoxysilane, 3- (m-aminophenoxy) propyltrimethoxysilane, 3- (N , N-dimethylamino) propyltriethoxysilane, 3- (N, N-dimethylamino) propyltrimethoxysilane, 3- (N-methylamino) propyltriethoxysilane, 3- (N-methylamino) propyltrimethoxy Silane, 3- (N-allylamino) propyltrimethoxysilane, 3,4-diaminobenzoic acid, 3-aminopropyldimethylethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyl Tris (methoxydiethoxy) silane, 3-amino Lopyldiisopropylethoxysilane, 3-isocyanatopropyltriethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-diethylaminopropyltrimethoxy Silane, 3-diethoxy (methyl) silylpropyl succinic anhydride, 3- (N, N-diethylaminopropyl) triethoxysilane, 3- (N, N-diethylaminopropyl) trimethoxysilane, 3- (N, N-dimethyl) Aminopropyl) diethoxymethylsilane, 3- (N, N-dimethylaminopropyl) triethoxysilane, 3- (N, N-dimethylaminopropyl) trimethoxysilane, 3-triethoxysilylpropyl succinic anhydride, 3- Trier Xylsilylpropylacetic anhydride, 3-triphenoxysilylpropyl succinic anhydride, 3-triphenoxysilylpropyl acetic anhydride, 3-trimethoxysilylpropylbenzothiazole tetrasulfide, 3-hexamethyleneiminopropyltriethoxysilane, 3-mercaptopropyl Trimethoxysilane, (3-triethoxysilylpropyl) diethylenetriamine, (3-trimethoxysilylpropyl) diethylenetriamine, 4,4′-bis (diethylamino) benzophenone, 4,4′-bis (dimethylamino) benzophenone, 4′- (Imidazol-1-yl) -acetophenone, 4- [3- (N, N-diglycidylamino) propyl] morpholine, 4-glycidyl-2,2,6,6-tetramethylpiperidinyloxy, 4-aminobu Tiltlyethoxysilane, 4-vinylpyridine, 4-morpholinoacetophenone, 4-morpholinobenzophenone, m-aminophenyltrimethoxysilane, N- (1,3-dimethylbutylidene) -3- (triethoxysilyl) -1- Propanamine, N- (1,3-dimethylbutylidene) -3- (trimethoxysilyl) -1-propanamine, N- (1-methylethylidene) -3- (triethoxysilyl) -1-propanamine, N- (2-aminoethyl) -3-aminopropylmethyldiethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxy Silane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-amino Ethyl) -11-aminoundecyltriethoxysilane, N- (2-aminoethyl) -11-aminoundecyltrimethoxysilane, N- (2-aminoethyl) -3-aminoisobutylmethyldiethoxysilane, N- (2-aminoethyl) -3-aminoisobutylmethyldimethoxysilane, N- (3-diethoxymethylsilylpropyl) succinimide, N- (3-triethoxysilylpropyl) -4,5-dihydroimidazole, N- (3 -Triethoxysilylpropyl) pyrrole, N- (3-trimethoxysilylpropyl) pyrrole, N-3- [amino (polypropyleneoxy)] aminopropyltrimethoxysilane, N- [5- (triethoxysilyl) -2- Aza 1-oxopentyl] caprolactam, N- [5- (trimethoxy Ryl) -2-aza-l-oxopentyl] caprolactam, N- (6-aminohexyl) aminomethyltriethoxysilane, N- (6-aminohexyl) aminomethyltrimethoxysilane, N-allyl-aza-2,2 -Diethoxysilacyclopentane, N-allyl-aza-2,2-dimethoxysilacyclopentane, N- (cyclohexylthio) phthalimide, Nn-butyl-aza-2,2-diethoxysilacyclopentane, N- n-butyl-aza-2,2-dimethoxysilacyclopentane, N, N, N ′, N′-tetraethylaminobenzophenone, N, N, N ′, N′-tetramethylthiourea, N, N, N ′, N'-tetramethylurea, N, N'-ethyleneurea, N, N'-diethylaminobenzophenone, N, N'-diethylaminobenzophenone N, N′-diethylaminobenzofuran, methyl N, N′-diethylcarbamate, N, N′-diethylurea, (N, N-diethyl-3-aminopropyl) triethoxysilane, (N, N-diethyl- 3-aminopropyl) trimethoxysilane, N, N-dioctyl-N′-triethoxysilylpropylurea, N, N-dioctyl-N′-trimethoxysilylpropylurea, methyl N, N-diethylcarbamate, N, N-diglycidylcyclohexylamine, N, N-dimethyl-o-toluidine, N, N-dimethylaminostyrene, N, N-diethylaminopropylacrylamide, N, N-dimethylaminopropylacrylamide, N-ethylaminoisobutyltriethoxysilane N-ethylaminoisobutyltrimethoxysilane, N Ethylaminoisobutylmethyldiethoxysilane, N-oxydiethylene-2-benzothiazolesulfenamide, N-cyclohexylaminopropyltriethoxysilane, N-cyclohexylaminopropyltrimethoxysilane, N-methylaminopropylmethyldimethoxysilane, N- Methylaminopropylmethyldiethoxysilane, N-vinylbenzylazacycloheptane, N-phenylpyrrolidone, N-phenylaminopropyltriethoxysilane, N-phenylaminopropyltrimethoxysilane, N-phenylaminomethyltriethoxysilane, N- Phenylaminomethyltrimethoxysilane, n-butylaminopropyltriethoxysilane, n-butylaminopropyltrimethoxysilane, N-methylaminopropyltrie Toxisilane, N-methylaminopropyltrimethoxysilane, N-methyl-2-piperidone, N-methyl-2-pyrrolidone, N-methyl-ε-caprolactam, N-methylindolinone, N-methylpyrrolidone, p- (2 -Dimethylaminoethyl) styrene, p-aminophenyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, (aminoethylamino) -3-isobutyldiethoxysilane, (aminoethyl) Amino) -3-isobutyldimethoxysilane, (aminoethylaminomethyl) phenethyltriethoxysilane, (aminoethylaminomethyl) phenethyltrimethoxysilane, acrylic acid, diethyl adipate, acetamidopropyltrimethoxysilane, aminophen Nyltrimethoxysilane, aminobenzophenone, ureidopropyltriethoxysilane, ureidopropyltrimethoxysilane, ethylene oxide, octadecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride, glycidoxypropyltriethoxysilane, glycidoxypropyltrimethoxysilane , Glycerol tristearate, chlorotriethoxysilane, chloropropyltriethoxysilane, chloropolydimethylsiloxane, chloromethyldiphenoxysilane, diallyldiphenyltin, diethylaminomethyltriethoxysilane, diethylaminomethyltrimethoxysilane, diethyl (glycidyl) amine, diethyl Dithiocarbamic acid 2-benzothiazoyl ester, diethoxydichlorosilane, (Rohexylaminomethyl) triethoxysilane, (cyclohexylaminomethyl) trimethoxysilane, diglycidylpolysiloxane, dichlorodiphenoxysilane, dicyclohexylcarbodiimide, divinylbenzene, diphenylcarbodiimide, diphenylcyanamide, diphenylmethane diisocyanate, diphenoxymethylchlorosilane, dibutyl Dichlorotin, dimethyl (acetoxy-methylsiloxane) polydimethylsiloxane, dimethylaminomethyltriethoxysilane, dimethylaminomethyltrimethoxysilane, dimethyl (methoxy-methylsiloxane) polydimethylsiloxane, dimethylimidazolidinone, dimethylethyleneurea, dimethyldi Chlorosilane, dimethylsulfoyl chloride, silsesquioxane, Sorbitan trioleate, sorbitan monolaurate, titanium tetrakis (2-ethylhexoxide), tetraethoxysilane, tetraglycidyl-1,3-bisaminomethylcyclohexane, tetraphenoxysilane, tetramethylthiuram disulfide, tetramethoxysilane , Triethoxyvinylsilane, tris (3-trimethoxysilylpropyl) cyanurate, triphenyl phosphate, triphenoxychlorosilane, triphenoxymethylsilicon, triphenoxymethylsilane, carbon dioxide, bis (triethoxysilylpropyl) amine, bis (trimethoxy Silylpropyl) amine, bis [3- (triethoxysilyl) propyl] ethylenediamine, bis [3- (trimethoxysilyl) propyl] ethyl Diamine, bis [3- (triethoxysilyl) propyl] urea, bis [(trimethoxysilyl) propyl] urea, bis (2-hydroxymethyl) -3-aminopropyltriethoxysilane, bis (2-hydroxymethyl)- 3-aminopropyltrimethoxysilane, bis (2-ethylhexanoate) tin, bis (2-methylbutoxy) methylchlorosilane, bis (3-triethoxysilylpropyl) tetrasulfide, bisdiethylaminobenzophenone, bisphenol A diglycidyl ether Bisphenoxyethanol fluorenediglycidyl ether, bis (methyldiethoxysilylpropyl) amine, bis (methyldimethoxysilylpropyl) -N-methylamine, hydroxymethyltriethoxysilane, vinyl tris 2-ethylhexyloxy) silane, vinylbenzyldiethylamine, vinylbenzyldimethylamine, vinylbenzyltributyltin, vinylbenzylpiperidine, vinylbenzylpyrrolidine, pyrrolidine, phenylisocyanate, phenylisothiocyanate, (phenylaminomethyl) methyldimethoxysilane, (phenyl) Aminomethyl) methyldiethoxysilane, phthalamide, hexamethylene diisocyanate, benzylidene aniline, polydiphenylmethane diisocyanate, polydimethylsiloxane, methyl-4-pyridyl ketone, methylcaprolactam, methyltriethoxysilane, methyltriphenoxysilane, lauryl Examples thereof include methyl thiopropionate and silicon tetrachloride. Among these, 3- (N, N-dimethylaminopropyl) trimethoxysilane, 3- (N, N-diethylaminopropyl) trimethoxysilane, 3- (N, N-dimethyl) are effective in improving performance. Aminopropyl) triethoxysilane, 3- (N, N-diethylaminopropyl) triethoxysilane, 3-glycidoxypropyltrimethoxysilane, 2- (4-pyridylethyl) triethoxysilane, N- (3-triethoxy) Silylpropyl) -4,5-dihydroimidazole, silicon tetrachloride and the like are preferable.
前記重合体の変性剤による変性は、前記重合体100重量部に対して0.01〜10重量部の変性剤を反応させ、例えばアニオン重合の場合、重合体における末端のアニオンと変性剤の官能基が反応することにより行うことができる。前記共重合体の少なくとも一方の末端が変性されていることが好ましく、両末端が変性されていることがより好ましい。 The modification of the polymer with a modifier is performed by reacting 0.01 to 10 parts by weight of the modifier with respect to 100 parts by weight of the polymer. For example, in the case of anionic polymerization, the terminal anion in the polymer and the function of the modifier are used. This can be done by reacting the group. It is preferable that at least one terminal of the copolymer is modified, and it is more preferable that both terminals are modified.
本発明においては、重合反応後に、必要に応じて、公知の老化防止剤や重合反応を停止する目的でアルコールなどを加えることができる。 In the present invention, after the polymerization reaction, a known anti-aging agent or alcohol or the like can be added for the purpose of stopping the polymerization reaction, if necessary.
前記重合体における窒素含有化合物の含有量は0.05重量%以上であることが好ましく、0.1重量%であることが特に好ましい。窒素含有化合物の含有量が0.05重量%未満では低燃費性およびウェットグリップ性能の改善効果が得られにくい傾向がある。また、含有量は30重量%以下であることが好ましく、20重量%以下であることが特に好ましい。含有量が30重量%を超えると高コストになってしまう傾向がある。 The content of the nitrogen-containing compound in the polymer is preferably 0.05% by weight or more, and particularly preferably 0.1% by weight. When the content of the nitrogen-containing compound is less than 0.05% by weight, it tends to be difficult to obtain the effect of improving the fuel efficiency and wet grip performance. The content is preferably 30% by weight or less, particularly preferably 20% by weight or less. If the content exceeds 30% by weight, the cost tends to increase.
前記重合体の重量平均分子量Mwは1.0×105以上であることが好ましく、2.0×105以上であることが特に好ましい。重量平均分子量が1.0×105未満ではヒステリシスロスが大きく十分な低燃費性が得られにくいだけでなく、耐摩耗性も低下する傾向がある。また、重量平均分子量Mwは2.0×106以下であることが好ましく、1.5×106以下であることが特に好ましい。2.0×106を超えると加工性が低下する傾向がある。 The weight average molecular weight Mw of the polymer is preferably 1.0 × 10 5 or more, and particularly preferably 2.0 × 10 5 or more. When the weight average molecular weight is less than 1.0 × 10 5 , not only is the hysteresis loss large and it is difficult to obtain sufficient fuel efficiency, but the wear resistance also tends to decrease. Further, the weight average molecular weight Mw is preferably 2.0 × 10 6 or less, and particularly preferably 1.5 × 10 6 or less. If it exceeds 2.0 × 10 6 , the workability tends to decrease.
本発明のゴム組成物においては、前記重合体を他のゴム成分とともに使用することができる。他のゴム成分としては、ジエン系ゴムを用いることが好ましい。ジエン系ゴムは、天然ゴム(NR)および/またはジエン系合成ゴムからなり、ジエン系合成ゴムとしては、たとえば、イソプレンゴム(IR)、ブタジエンゴム(BR)、スチレンブタジエンゴム(SBR)、アクリロニトリルブタジエンゴム(NBR)、クロロプレンゴム(CR)、ブチルゴム(IIR)などがあげられる。中でも、グリップ性能および耐摩耗性をバランスよく示すことから、NR、BR、SBRが好ましい。これらのゴムは単独で用いてもよく、2種以上を組み合わせてもよい。 In the rubber composition of the present invention, the polymer can be used together with other rubber components. As another rubber component, it is preferable to use a diene rubber. The diene rubber is composed of natural rubber (NR) and / or a diene synthetic rubber. Examples of the diene synthetic rubber include isoprene rubber (IR), butadiene rubber (BR), styrene butadiene rubber (SBR), and acrylonitrile butadiene. Examples thereof include rubber (NBR), chloroprene rubber (CR), and butyl rubber (IIR). Among these, NR, BR, and SBR are preferable because grip performance and wear resistance are well-balanced. These rubbers may be used alone or in combination of two or more.
本発明のゴム組成物において、前記重合体の配合量は、ゴム成分100重量%中、5重量%以上が好ましく、10重量%以上がより好ましい。配合量が5重量%未満であると低燃費性およびウェットグリップ性能の改善効果が得られにくい傾向がある。上限は特に限定されないが、90重量%以下が好ましく、80重量%以下がより好ましい。90重量%を超えると、コストが高くなる傾向がある。 In the rubber composition of the present invention, the blending amount of the polymer is preferably 5% by weight or more and more preferably 10% by weight or more in 100% by weight of the rubber component. If the blending amount is less than 5% by weight, it tends to be difficult to obtain an effect of improving fuel economy and wet grip performance. Although an upper limit is not specifically limited, 90 weight% or less is preferable and 80 weight% or less is more preferable. If it exceeds 90% by weight, the cost tends to increase.
本発明のゴム組成物においては補強剤としてカーボンブラックおよび/またはシリカを配合することが好ましい。 In the rubber composition of the present invention, it is preferable to blend carbon black and / or silica as a reinforcing agent.
カーボンブラックのチッ素吸着比表面積(N2SA)は、80m2/g以上が好ましく、特には100m2/g以上であることが好ましい。カーボンブラックのN2SAが80m2/g未満では十分なウェットグリップ性能が得られず、また耐摩耗性が低下する傾向がある。また、カーボンブラックのN2SAは280m2/g以下が好ましく、250m2/g以下がより好ましい。カーボンブラックのN2SAが280m2/gをこえると、分散性に劣り、耐摩耗性が低下する傾向がある。 The nitrogen adsorption specific surface area (N 2 SA) of carbon black is preferably 80 m 2 / g or more, and particularly preferably 100 m 2 / g or more. If the N 2 SA of the carbon black is less than 80 m 2 / g, sufficient wet grip performance cannot be obtained, and wear resistance tends to decrease. Further, N 2 SA of carbon black is preferably 280 m 2 / g or less, and more preferably 250 m 2 / g or less. When N 2 SA of carbon black exceeds 280 m 2 / g, the dispersibility is inferior and the wear resistance tends to be lowered.
カーボンブラックの含有量は、ゴム成分100重量部に対して5重量部以上が好ましく、10重量部以上がより好ましい。カーボンブラックの含有量が5重量部未満では、耐摩耗性が低下する傾向がある。一方、カーボンブラックの含有量は150重量部以下が好ましく、100重量部以下がより好ましい。カーボンブラックの含有量が150重量部をこえると、加工性が悪化する傾向がある。カーボンブラックは単独で用いてもよく、2種以上を組み合わせて用いてもよい。 The content of carbon black is preferably 5 parts by weight or more and more preferably 10 parts by weight or more with respect to 100 parts by weight of the rubber component. When the content of carbon black is less than 5 parts by weight, the wear resistance tends to decrease. On the other hand, the carbon black content is preferably 150 parts by weight or less, and more preferably 100 parts by weight or less. If the carbon black content exceeds 150 parts by weight, processability tends to deteriorate. Carbon black may be used alone or in combination of two or more.
シリカのチッ素吸着比表面積(N2SA)は、50m2/g以上であることが好ましく、特には80m2/g以上であることが好ましい。また、300m2/g以下であることが好ましく、特には250m2/g以下であることが好ましい。チッ素吸着比表面積が50m2/g未満のシリカでは補強効果が小さく耐摩耗性が低下する傾向があり、300m2/gをこえるシリカでは分散性が悪く、ヒステリシスロスが増大し燃費性能が低下する傾向がある。 The nitrogen adsorption specific surface area (N 2 SA) of silica is preferably 50 m 2 / g or more, and particularly preferably 80 m 2 / g or more. Moreover, it is preferable that it is 300 m < 2 > / g or less, and it is especially preferable that it is 250 m < 2 > / g or less. Silica with a nitrogen adsorption specific surface area of less than 50 m 2 / g has a small reinforcing effect and tends to decrease wear resistance, and silica exceeding 300 m 2 / g has poor dispersibility, increases hysteresis loss, and decreases fuel efficiency. Tend to.
シリカの配合量は、ゴム成分100重量部に対して、5重量部以上が好ましく、10重量部以上がより好ましい。シリカの配合量が5重量部未満であると耐摩耗性が十分でない傾向がある。一方、シリカの配合量は、150重量部以下が好ましく、100重量部以下がより好ましい。シリカの配合量が150重量部をこえると、加工性が悪化する傾向がある。シリカは単独で用いてもよく、2種以上を組み合わせて用いてもよい。 The amount of silica is preferably 5 parts by weight or more, and more preferably 10 parts by weight or more with respect to 100 parts by weight of the rubber component. When the amount of silica is less than 5 parts by weight, the wear resistance tends to be insufficient. On the other hand, the blending amount of silica is preferably 150 parts by weight or less, and more preferably 100 parts by weight or less. If the amount of silica exceeds 150 parts by weight, the processability tends to deteriorate. Silica may be used alone or in combination of two or more.
シリカを配合する場合には、シランカップリング剤を併用しても良い。
シランカップリング剤としては、例えば、ビス(3−トリエトキシシリルプロピル)テトラスルフィド、ビス(3−トリエトキシシリルプロピル)トリスルフィド、ビス(3−トリエトキシシリルプロピル)ジスルフィド、ビス(2−トリエトキシシリルエチル)テトラスルフィド、ビス(3−トリメトキシシリルプロピル)テトラスルフィド、ビス(2−トリメトキシシリルエチル)テトラスルフィド、3−メルカプトプロピルトリメトキシシラン、3−メルカプトプロピルトリエトキシシラン、2−メルカプトエチルトリメトキシシラン、2−メルカプトエチルトリエトキシシラン、3−トリメトキシシリルプロピル−N,N−ジメチルチオカルバモイルテトラスルフィド、3−トリエトキシシリルプロピル−N,N−ジメチルチオカルバモイルテトラスルフィド、2−トリエトキシシリルエチル−N,N−ジメチルチオカルバモイルテトラスルフィド、3−トリメトキシシリルプロピルベンゾチアゾールテトラスルフィド、3−トリエトキシシリルプロピルベンゾチアゾリルテトラスルフィド、3−トリエトキシシリルプロピルメタクリレートモノスルフィド、3−トリメトキシシリルプロピルメタクリレートモノスルフィド、ビス(3−ジエトキシメチルシリルプロピル)テトラスルフィド、3−メルカプトプロピルジメトキシメチルシラン、ジメトキシメチルシリルプロピル−N,N−ジメチルチオカルバモイルテトラスルフィド、ジメトキシメチルシリルプロピルベンゾチアゾールテトラスルフィドなどがあげられる。なかでも、補強性改善効果などの点から、ビス(3−トリエトキシシリルプロピル)テトラスルフィドおよび3−トリメトキシシリルプロピルベンゾチアゾリルテトラスルフィドが好ましい。これらのシランカップリング剤は単独で用いてもよく、2種以上を組み合わせて用いてもよい。
When silica is blended, a silane coupling agent may be used in combination.
Examples of the silane coupling agent include bis (3-triethoxysilylpropyl) tetrasulfide, bis (3-triethoxysilylpropyl) trisulfide, bis (3-triethoxysilylpropyl) disulfide, and bis (2-triethoxy). Silylethyl) tetrasulfide, bis (3-trimethoxysilylpropyl) tetrasulfide, bis (2-trimethoxysilylethyl) tetrasulfide, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 2-mercaptoethyl Trimethoxysilane, 2-mercaptoethyltriethoxysilane, 3-trimethoxysilylpropyl-N, N-dimethylthiocarbamoyl tetrasulfide, 3-triethoxysilylpropyl-N, N-dimethylthiocarb Moyl tetrasulfide, 2-triethoxysilylethyl-N, N-dimethylthiocarbamoyl tetrasulfide, 3-trimethoxysilylpropylbenzothiazole tetrasulfide, 3-triethoxysilylpropylbenzothiazolyl tetrasulfide, 3-triethoxysilyl Propyl methacrylate monosulfide, 3-trimethoxysilylpropyl methacrylate monosulfide, bis (3-diethoxymethylsilylpropyl) tetrasulfide, 3-mercaptopropyldimethoxymethylsilane, dimethoxymethylsilylpropyl-N, N-dimethylthiocarbamoyl tetrasulfide And dimethoxymethylsilylpropylbenzothiazole tetrasulfide. Of these, bis (3-triethoxysilylpropyl) tetrasulfide and 3-trimethoxysilylpropylbenzothiazolyl tetrasulfide are preferable from the viewpoint of improving reinforcing properties. These silane coupling agents may be used alone or in combination of two or more.
シランカップリング剤の配合量は、前記シリカ100重量部に対して1重量部以上であることが好ましく、2重量部以上であることがより好ましい。シランカップリング剤の配合量が1重量部未満では、未加硫ゴム組成物の粘度が高く加工性が悪くなる傾向がある。また、シランカップリング剤の配合量は、前記シリカ100重量部に対し、20重量部以下であることが好ましく、15重量部以下であることがより好ましい。シランカップリング剤の配合量が20重量部をこえると、その配合量ほどのシランカップリング剤の配合効果が得られず、コストが高くなる傾向がある。 The compounding amount of the silane coupling agent is preferably 1 part by weight or more and more preferably 2 parts by weight or more with respect to 100 parts by weight of the silica. When the amount of the silane coupling agent is less than 1 part by weight, the viscosity of the unvulcanized rubber composition tends to be high and the processability tends to be poor. Moreover, the compounding amount of the silane coupling agent is preferably 20 parts by weight or less and more preferably 15 parts by weight or less with respect to 100 parts by weight of the silica. If the blending amount of the silane coupling agent exceeds 20 parts by weight, the blending effect of the silane coupling agent as much as the blending amount cannot be obtained, and the cost tends to increase.
本発明のゴム組成物には、その他の補強剤、加硫剤、加硫促進剤、各種オイル、老化防止剤、軟化剤、可塑剤などのタイヤ用または一般のゴム組成物用に配合される各種配合剤および添加剤を配合することができる。また、これらの配合剤、添加剤の含有量も一般的な量とすることができる。 In the rubber composition of the present invention, other reinforcing agents, vulcanizing agents, vulcanization accelerators, various oils, anti-aging agents, softeners, plasticizers and the like are blended for tires or general rubber compositions. Various compounding agents and additives can be blended. Moreover, the content of these compounding agents and additives can also be set to general amounts.
また、本発明は、前記ゴム組成物を用いて作製したタイヤに関し、該タイヤは、本発明のゴム組成物を用いて通常の方法によって製造される。すなわち、必要に応じて前記各種薬品を配合した本発明のゴム組成物を未加硫の段階でタイヤの各部材の形状に合わせて押し出し加工し、タイヤ成型機上にて通常の方法にて成形し、未加硫タイヤを形成する。この未加硫タイヤを加硫機中で加熱加圧してタイヤを得る。このようにして得られた本発明のタイヤは、低発熱性とウェットグリップ性能において優れたバランスを示すものである。タイヤの部材の中でも、特にトレッド部に使用することが好ましい。 Moreover, this invention relates to the tire produced using the said rubber composition, This tire is manufactured by a normal method using the rubber composition of this invention. That is, if necessary, the rubber composition of the present invention blended with the above various chemicals is extruded in accordance with the shape of each member of the tire at an unvulcanized stage, and molded by a normal method on a tire molding machine. And an unvulcanized tire is formed. This unvulcanized tire is heated and pressurized in a vulcanizer to obtain a tire. The tire of the present invention thus obtained exhibits an excellent balance in low heat buildup and wet grip performance. Among tire members, it is particularly preferable to use the tread portion.
実施例にもとづいて、本発明を具体的に説明するが、本発明はこれらのみに限定されるものではない。 The present invention will be specifically described based on examples, but the present invention is not limited to these examples.
以下に、窒素含有化合物であるモノマー(1)〜(10)の合成で用いた各種薬品について説明する。
シクロヘキサン:関東化学(株)製シクロヘキサン
ピロリジン:関東化学(株)製ピロリジン
ヘキサメチレンイミン:関東化学(株)製ヘキサメチレンイミン
モルホリン:関東化学(株)製モルホリン
チアゾリジン:関東化学(株)製チアゾリジン
4−ピペリジノピペリジン:関東化学(株)製4−ピペリジノピペリジン
4−ジメチルアミノ−2,2,6,6−テトラメチルピペリジン:シグマアルドリッチ社製4−ジメチルアミノ−2,2,6,6−テトラメチルピペリジン
ジプロピルアミン:シグマアルドリッチ社製ジプロピルアミン
ジフェニルアミン:シグマアルドリッチ社製ジフェニルアミン
2,2’−ジピリジルアミン:シグマアルドリッチ社製2,2’−ジピリジルアミン
ジビニルベンゼン:シグマアルドリッチ社製ジビニルベンゼン
1,3−ジイソプロペニルベンゼン:シグマアルドリッチ社製1,3−ジイソプロペニルベンゼン
1.6M n−ブチルリチウムヘキサン溶液:関東化学(株)製1.6M n−ブチルリチウムヘキサン溶液
イソプロパノール:関東化学(株)製イソプロパノール
Hereinafter, various chemicals used in the synthesis of monomers (1) to (10) which are nitrogen-containing compounds will be described.
Cyclohexane: cyclohexane pyrrolidine manufactured by Kanto Chemical Co., Ltd .: pyrrolidine hexamethyleneimine manufactured by Kanto Chemical Co., Ltd .: hexamethyleneimine morpholine manufactured by Kanto Chemical Co., Ltd .: morpholine thiazolidine manufactured by Kanto Chemical Co., Ltd .: thiazolidine 4 manufactured by Kanto Chemical Co., Ltd. -Piperidinopiperidine: 4-piperidinopiperidine 4-dimethylamino-2,2,6,6-tetramethylpiperidine manufactured by Kanto Chemical Co., Ltd .: 4-dimethylamino-2,2,6 manufactured by Sigma-Aldrich 6-tetramethylpiperidine dipropylamine: Sigma-Aldrich dipropylamine diphenylamine: Sigma-Aldrich diphenylamine 2,2′-dipyridylamine: Sigma-Aldrich 2,2′-dipyridylamine divinylbenzene: Sigma-Aldrich divinylben 1,3-diisopropenylbenzene: 1,3-diisopropenylbenzene 1.6M n-butyllithium hexane solution manufactured by Sigma-Aldrich, Inc. 1.6M n-butyllithium hexane solution manufactured by Kanto Chemical Co., Inc. Isopropanol: Kanto Chemical Co., Ltd. Isopropanol
製造例1(モノマー(1)の合成)
十分に窒素置換した100ml容器に、シクロヘキサン50ml、ピロリジン4.1ml(3.6g)、ジビニルベンゼン8.9ml(6.5g)を加え、0℃にて1.6M n−ブチルリチウムヘキサン溶液0.7mlを加えて攪拌した。1時間後、イソプロパノールを加えて反応を停止させ、抽出・精製を行うことでモノマー(1)を得た。
Production Example 1 (Synthesis of Monomer (1))
To a 100 ml container thoroughly purged with nitrogen, 50 ml of cyclohexane, 4.1 ml (3.6 g) of pyrrolidine and 8.9 ml (6.5 g) of divinylbenzene were added, and a 1.6 M n-butyllithium hexane solution at 0 ° C. 7 ml was added and stirred. After 1 hour, isopropanol was added to stop the reaction, and extraction / purification was performed to obtain a monomer (1).
製造例2〜10(モノマー(2)〜(10)の合成)
表1に示す処方に従って、モノマー(1)と同様の処方にてモノマー(2)〜(10)を得た。
Production Examples 2 to 10 (Synthesis of monomers (2) to (10))
In accordance with the formulation shown in Table 1, monomers (2) to (10) were obtained with the same formulation as monomer (1).
以下に、重合体(1)〜(38)の合成で用いた各種薬品について説明する。
シクロヘキサン:関東化学(株)製シクロヘキサン
スチレン:関東化学(株)製スチレン
ブタジエン:高千穂化学工業(株)製1,3−ブタジエン
テトラメチルエチレンジアミン:関東化学(株)製N,N,N’,N’−テトラメチルエチレンジアミン
1.6M n−ブチルリチウムヘキサン溶液:関東化学(株)製1.6M n−ブチルリチウムヘキサン溶液
1.0M 四塩化ケイ素:シグマアルドリッチ社製の四塩化ケイ素をシクロヘキサンで1.0Mに希釈したもの
1.0M 四塩化すず:シグマアルドリッチ社製の四塩化すずをシクロヘキサンで1.0Mに希釈したもの
変性剤(1):前述のモノマー(1)
変性剤(2):信越シリコーン(株)製のテトラエトキシシラン
変性剤(3):アヅマックス社製の3−(N,N−ジメチルアミノプロピル)トリメトキシシラン
変性剤(4):アヅマックス社製の3−グリシドキシプロピルトリメトキシシラン
変性剤(5):アヅマックス社製の3−トリエトキシシリルプロピル無水コハク酸
変性剤(6):アヅマックス社製の2−(4−ピリジルエチル)トリエトキシシラン
変性剤(7):アヅマックス社製のN−(3−トリエトキシシリルプロピル)4,5−ジヒドロイミダゾール
変性剤(8):アヅマックス社製の11−(スクシンイミジロキシ)ウンデシルジメチルエトキシシラン
変性剤(9):アヅマックス社製の3−イソシアネートプロピルトリエトキシシラン
変性剤(10):アヅマックス社製のトリス(3−トリメトキシシリルプロピル)シアヌレート
イソプロパノール:関東化学(株)製イソプロパノール
Hereinafter, various chemicals used in the synthesis of the polymers (1) to (38) will be described.
Cyclohexane: Kanto Chemical Co., Ltd. cyclohexane styrene: Kanto Chemical Co., Ltd. styrene butadiene: Takachiho Chemical Industry Co., Ltd. 1,3-butadiene tetramethylethylenediamine: Kanto Chemical Co., Ltd. N, N, N ', N '-Tetramethylethylenediamine 1.6M n-butyllithium hexane solution: 1.6M n-butyllithium hexane solution 1.0M manufactured by Kanto Chemical Co., Ltd. Silicon tetrachloride: Silicon tetrachloride manufactured by Sigma-Aldrich Co. Diluted to 0M 1.0M Tin tetrachloride: Diluted tin tetrachloride made by Sigma-Aldrich to 1.0M with cyclohexane Modifier (1): Monomer (1)
Modifier (2): Tetraethoxysilane modifier manufactured by Shin-Etsu Silicone Co., Ltd. (3): 3- (N, N-dimethylaminopropyl) trimethoxysilane modifier manufactured by AMAX Co. (4): manufactured by AMAX Co. 3-glycidoxypropyltrimethoxysilane modifier (5): Atrimax 3-triethoxysilylpropyl succinic anhydride modifier (6): 2-max (4-pyridylethyl) triethoxysilane modified by Amax Agent (7): N- (3-triethoxysilylpropyl) 4,5-dihydroimidazole modifier manufactured by AMAX Co. (8): 11- (succinimidyloxy) undecyldimethylethoxysilane modifier manufactured by AMAX Co. (9): Amax Co. 3-isocyanatopropyltriethoxysilane modifier (10): Amax Made in tris (3-trimethoxysilylpropyl) cyanurate isopropanol: Kanto Chemical Co. isopropanol
実施例1(重合体(1)の合成)
十分に窒素置換した1000ml耐圧製容器に、シクロヘキサン600ml、スチレン12.6ml(11.4g)、ブタジエン71.0ml(44.0g)、モノマー(1)0.29g、テトラメチルエチレンジアミン0.11mlを加え、40℃で1.6M n−ブチルリチウムヘキサン溶液0.2mlを加えて撹拌した。3時間後、イソプロパノール2mlを加えて重合を停止させた。反応溶液に2,6−tert−ブチル−p−クレゾール1gを添加後、メタノールで再沈殿処理を行い、加熱乾燥させて重合体(1)を得た。
Example 1 (Synthesis of polymer (1))
To a 1000 ml pressure vessel fully purged with nitrogen, add 600 ml of cyclohexane, 12.6 ml (11.4 g) of styrene, 71.0 ml (44.0 g) of butadiene, 0.29 g of monomer (1) and 0.11 ml of tetramethylethylenediamine. Then, 0.2 ml of 1.6M n-butyllithium hexane solution was added at 40 ° C. and stirred. After 3 hours, 2 ml of isopropanol was added to stop the polymerization. After adding 1 g of 2,6-tert-butyl-p-cresol to the reaction solution, reprecipitation treatment was performed with methanol, followed by heating and drying to obtain polymer (1).
実施例2〜14および比較例1(重合体(2)〜(15)の合成)
表2に示す処方に従って、重合体(1)と同様の処方にて重合体(2)〜(15)を得た。
Examples 2 to 14 and Comparative Example 1 (Synthesis of polymers (2) to (15))
According to the formulation shown in Table 2, polymers (2) to (15) were obtained with the same formulation as the polymer (1).
実施例15(重合体(16)の合成)
十分に窒素置換した1000ml耐圧製容器に、シクロヘキサン600ml、スチレン12.6ml(11.4g)、ブタジエン71.0ml(44.0g)、モノマー(1)0.29g、テトラメチルエチレンジアミン0.05mlを加え、40℃で1.6M n−ブチルリチウムヘキサン溶液0.1mlを加えて撹拌した。3時間後、変性剤(3)を0.5ml(0.47g)加えて攪拌した。1時間後、イソプロパノール2mlを加えて重合を停止させた。反応溶液に2,6−tert−ブチル−p−クレゾール1gを添加後、メタノールで再沈殿処理を行い、加熱乾燥させて重合体(16)を得た。
Example 15 (Synthesis of polymer (16))
To a 1000 ml pressure vessel fully purged with nitrogen, add 600 ml of cyclohexane, 12.6 ml (11.4 g) of styrene, 71.0 ml (44.0 g) of butadiene, 0.29 g of monomer (1), and 0.05 ml of tetramethylethylenediamine. Then, 0.1 ml of 1.6M n-butyllithium hexane solution was added at 40 ° C. and stirred. Three hours later, 0.5 ml (0.47 g) of the modifier (3) was added and stirred. After 1 hour, 2 ml of isopropanol was added to terminate the polymerization. After adding 1 g of 2,6-tert-butyl-p-cresol to the reaction solution, reprecipitation treatment was performed with methanol, followed by heating and drying to obtain polymer (16).
実施例16〜36および比較例2(重合体(17)〜(38)の合成)
表3に示す処方に従って、重合体(16)と同様の処方にて重合体(17)〜(38)を得た。
Examples 16 to 36 and Comparative Example 2 (Synthesis of polymers (17) to (38))
According to the formulation shown in Table 3, polymers (17) to (38) were obtained with the same formulation as the polymer (16).
(重量平均分子量Mwの測定)
重量平均分子量Mwは、東ソー(株)製GPC−8000シリーズの装置を用い、検知器として示差屈折計を用い、分子量は標準ポリスチレンにより校正した。
(Measurement of weight average molecular weight Mw)
For the weight average molecular weight Mw, a GPC-8000 series apparatus manufactured by Tosoh Corporation was used, a differential refractometer was used as a detector, and the molecular weight was calibrated with standard polystyrene.
(重合体中の窒素含有化合物誘導体モノマー量の測定)
重合体中の窒素含有化合物誘導体モノマー量は、日本電子(株)製JNM−ECAシリーズのNMR装置を用いて測定した。
(Measurement of amount of nitrogen-containing compound derivative monomer in polymer)
The amount of the nitrogen-containing compound derivative monomer in the polymer was measured using a JNM-ECA series NMR apparatus manufactured by JEOL Ltd.
実施例37〜76および比較例3、4
以下に、実施例37〜76および比較例3、4で用いた各種薬品について説明する。
NR:RSS#3
カーボンブラック:キャボットジャパン(株)製のショウブラックN220(チッ素吸着比表面積(N2SA):125m2/g)
シリカ:デグッサ社製のウルトラシルVN3(チッ素吸着比表面積(N2SA):210m2/g)
シランカップリング剤:デグッサ社製のSi69
アロマオイル:(株)ジャパンエナジー製のJOMOプロセスX140
ステアリン酸:日油(株)製のステアリン酸
酸化亜鉛:三井金属鉱業(株)製の亜鉛華1号
老化防止剤:大内新興化学工業(株)製のノクラック6C(N−1,3−ジメチルブチル−N’−フェニル−p−フェニレンジアミン)
ワックス:大内新興化学工業(株)製のサンノックワックス
硫黄:鶴見化学(株)製の粉末硫黄
加硫促進剤1:大内新興化学工業(株)製のノクセラーCZ
加硫促進剤2:大内新興化学工業(株)製のノクセラーD
Examples 37 to 76 and Comparative Examples 3 and 4
The various chemicals used in Examples 37 to 76 and Comparative Examples 3 and 4 are described below.
NR: RSS # 3
Carbon black: Show black N220 manufactured by Cabot Japan Co., Ltd. (nitrogen adsorption specific surface area (N 2 SA): 125 m 2 / g)
Silica: Ultrasil VN3 manufactured by Degussa (Nitrogen adsorption specific surface area (N 2 SA): 210 m 2 / g)
Silane coupling agent: Si69 manufactured by Degussa
Aroma oil: JOMO process X140 manufactured by Japan Energy Co., Ltd.
Stearic acid: Zinc stearate manufactured by NOF Corporation: Zinc Hua 1 anti-aging agent manufactured by Mitsui Mining & Smelting Co., Ltd .: NOCRACK 6C (N-1,3- Dimethylbutyl-N′-phenyl-p-phenylenediamine)
Wax: Sunnock wax manufactured by Ouchi Shinsei Chemical Co., Ltd. Sulfur: Powder sulfur vulcanization accelerator manufactured by Tsurumi Chemical Co., Ltd. 1: Noxeller CZ manufactured by Ouchi Shinsei Chemical Co., Ltd.
Vulcanization accelerator 2: Noxeller D from Ouchi Shinsei Chemical Co., Ltd.
表4及び表5に示す配合処方(配合量の単位はすべて重量部)にしたがって、混練り配合し、各種供試ゴム組成物を得た。これらの配合物を170℃で20分間プレス加硫して加硫物を得て、これらについて以下に示す試験方法により低燃費性およびウェットグリップ性能を評価した。 According to the compounding formulations shown in Tables 4 and 5 (all the unit of compounding is parts by weight), they were kneaded and compounded to obtain various test rubber compositions. These blends were press vulcanized at 170 ° C. for 20 minutes to obtain vulcanizates, which were evaluated for fuel economy and wet grip performance by the following test methods.
(低燃費性(転がり抵抗))
(株)上島製作所製スペクトロメーターを用いて、動的歪振幅1%、周波数10Hz、温度60℃でtanδを測定した。tanδの逆数の値について比較例3又は4を100として指数表示した。数値が大きいほど転がり抵抗が小さく、低燃費であることを示している。
(Low fuel consumption (rolling resistance))
Using a spectrometer manufactured by Ueshima Seisakusho, tan δ was measured at a dynamic strain amplitude of 1%, a frequency of 10 Hz, and a temperature of 60 ° C. The reciprocal value of tan δ was expressed as an index with Comparative Example 3 or 4 as 100. The larger the value, the lower the rolling resistance and the lower the fuel consumption.
(ウェットグリップ性能(1))
(株)上島製作所製フラットベルト式摩擦試験機(FR5010型)を用いてグリップ性能を評価した。幅20mm、直径100mmの円筒形のゴム試験片を用い、速度20km/時間、荷重4kgf、路面温度20℃の条件で、路面に対するサンプルのスリップ率を0〜70%まで変化させ、その際に検出される摩擦係数の最大値を読みとった。比較例3又は4を100として指数表示した。指数が大きいほどウェットグリップ性能が高いことを示す。
(Wet grip performance (1))
Grip performance was evaluated using a flat belt friction tester (FR5010 type) manufactured by Ueshima Seisakusho. Using a cylindrical rubber test piece with a width of 20 mm and a diameter of 100 mm, the slip ratio of the sample with respect to the road surface is changed from 0 to 70% under the conditions of a speed of 20 km / hour, a load of 4 kgf, and a road surface temperature of 20 ° C. The maximum value of the coefficient of friction to be used was read. The comparative example 3 or 4 was set as 100 and displayed as an index. The larger the index, the higher the wet grip performance.
(ウェットグリップ性能(2))
前記未加硫ゴム組成物をトレッドの形状に成形し、他のタイヤ部材とともに貼り合わせて未加硫タイヤを形成し、170℃の条件下で10分間プレス加硫し、タイヤ(サイズ195/65R15)を製造した。水を撒いて湿潤路面としたテストコースにて、タイヤを排気量2000ccの国産FR車に装着し、速度70km/hで制動し、タイヤに制動をかけてから停車するまでの走行距離(制動距離)を測定し、その距離の逆数の値を比較例3又は4を100として、それぞれ指数表示した。数値が大きいほどウェットグリップ性能が高いことを示す。
(Wet grip performance (2))
The unvulcanized rubber composition is molded into a tread shape and bonded together with other tire members to form an unvulcanized tire, press vulcanized at 170 ° C. for 10 minutes, and a tire (size 195 / 65R15 ) Was manufactured. On a test course with wet water and wet road surface, the tire is mounted on a 2000cc domestic FR vehicle, braked at a speed of 70km / h, and the distance traveled from braking the tire to stopping (braking distance) ) Was measured, and the value of the reciprocal of the distance was displayed as an index with Comparative Example 3 or 4 as 100. It shows that wet grip performance is so high that a numerical value is large.
表4に示すように、窒素含有化合物を含んだ重合体を含有した実施例37〜52のゴム組成物は、比較例3のゴム組成物に比べて、低燃費性とウェットグリップ性能のバランスに優れたゴム組成物であることが明らかとなった。 As shown in Table 4, the rubber compositions of Examples 37 to 52 containing a polymer containing a nitrogen-containing compound have a balance between low fuel consumption and wet grip performance as compared with the rubber composition of Comparative Example 3. It was revealed that the rubber composition was excellent.
表5に示すように、主鎖に特定の窒素含有化合物を有し、さらに末端を特定の官能基で変性した重合体を含有した実施例53〜76のゴム組成物は、窒素含有化合物を含まず、末端が変性されていない重合体を配合した比較例4のゴム組成物に比べて、低燃費性とウェットグリップ性能のバランスに優れたゴム組成物であることが明らかとなった。 As shown in Table 5, the rubber compositions of Examples 53 to 76 each having a specific nitrogen-containing compound in the main chain and further containing a polymer having a terminal modified with a specific functional group include the nitrogen-containing compound. As a result, it was revealed that the rubber composition was excellent in the balance between low fuel consumption and wet grip performance as compared with the rubber composition of Comparative Example 4 in which a polymer whose terminal was not modified was blended.
Claims (8)
で表される窒素含有化合物とを共重合して得られる重合体。 Conjugated diene compounds and / or aromatic vinyl compounds and the following general formula
A polymer obtained by copolymerizing a nitrogen-containing compound represented by the formula:
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